Michaelis–Arbuzov reaction - Revision history

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	[[file:Michaelis-Arbuzov Reaction Mechanism.png\|center\|600px\|The mechanism of the Michaelis–Arbuzov reaction]]		[[file:Michaelis-Arbuzov Reaction Mechanism.png\|center\|600px\|The mechanism of the Michaelis–Arbuzov reaction]]

	The Michaelis–Arbuzov reaction is initiated with the [[SN2 reaction\|S<sub>N</sub>2 attack]] of the [[nucleophilic]] phosphorus species ('''1''' - A phosphite) with the [[electrophilic]] alkyl halide ('''2''') to give a [[phosphonium salt]] as an intermediate ('''3'''). These intermediates are occasionally stable enough to be isolated, such as for triaryl phosphites which do not react to form the phosphonate without thermal cleavage of the intermediate (200 °C), or cleavage by alcohols or bases. The displaced [[halide]] anion then usually reacts via another S<sub>N</sub>2 reaction on one of the R<sub>1</sub> carbons, displacing the oxygen atom to give the desired phosphonate ('''4''') and another alkyl halide ('''5'''). This has been supported by the observation that chiral R<sub>1</sub> groups experience inversion of configuration at the carbon center attacked by the halide anion. This is what is expected of an S<sub>N</sub>2 reaction.<ref>{{cite journal \|author1=Gerrard, W. \|author2=Green, W. J. \| journal = J. Chem. Soc. \| year = 1951 \| pages = 2550\| doi = 10.1039/jr9510002550\| title = 568. Mechanism of the formation of dialkyl alkylphosphonates}}</ref> Evidence also exists for a [[carbocation]] based mechanism of dealkylation similar to an [[SN1 reaction\|S<sub>N</sub>1 reaction]], where the R<sub>1</sub> group initially dissociates from the phosphonium salt followed by attack of the anion.<ref name=":0" /> ~~Phosphite esters with tertiary alkyl halide groups can undergo the reaction, which would be unexpected if only~~ an S<sub>N</sub>2 ~~mechanism was operating. Further support for this~~ S<sub>N</sub>1 ~~type mechanism comes from the use of the Arbuzov reaction in the synthesis of~~ [[~~neopentyl~~]] halides, a class of compounds that are notoriously unreactive towards S<sub>N</sub>2 reactions. Based on the principle of [[microscopic reversibility]], the inert nature of the neopentyl halides towards the S<sub>N</sub>2 reaction indicates that an S<sub>N</sub>2 reaction is unlikely to ~~be the mechanism for the synthesis of~~ the ~~neopentyl halides in this~~ reaction. ~~Substrates that cannot react through an S~~<~~sub~~>~~N</sub>2 pathway or an S<sub>N</sub>1 pathway generally do not react, which include [[vinyl group~~\|~~vinyl]] and [[aryl]] groups. For example~~, ~~the triaryl phosphites mentioned above generally do not react because they form stable phosphonium salts. Since aryl groups do not undergo S<sub>N</sub>1~~ and ~~S<sub>N</sub>2 type mechanisms, triaryl phosphites lack a low energy pathway for decomposition~~ of the ~~phosphonium salt~~. ~~An [[allylic rearrangement]] mechanism ('''S<sub>N~~</~~sub~~>~~2'''') has also been implicated in [[Allyl group\|allyl]] and [[propargyl]] halides.~~		The Michaelis–Arbuzov reaction is initiated with the [[SN2 reaction\|S<sub>N</sub>2 attack]] of the [[nucleophilic]] phosphorus species ('''1''' - A phosphite) with the [[electrophilic]] alkyl halide ('''2''') to give a [[phosphonium salt]] as an intermediate ('''3'''). These intermediates are occasionally stable enough to be isolated, such as for triaryl phosphites which do not react to form the phosphonate without thermal cleavage of the intermediate (200 °C), or cleavage by alcohols or bases. The displaced [[halide]] anion then usually reacts via another S<sub>N</sub>2 reaction on one of the R<sub>1</sub> carbons, displacing the oxygen atom to give the desired phosphonate ('''4''') and another alkyl halide ('''5'''). This has been supported by the observation that chiral R<sub>1</sub> groups experience inversion of configuration at the carbon center attacked by the halide anion. This is what is expected of an S<sub>N</sub>2 reaction.<ref>{{cite journal \|author1=Gerrard, W. \|author2=Green, W. J. \| journal = J. Chem. Soc. \| year = 1951 \| pages = 2550\| doi = 10.1039/jr9510002550\| title = 568. Mechanism of the formation of dialkyl alkylphosphonates}}</ref> Evidence also exists for a [[carbocation]] based mechanism of dealkylation similar to an [[SN1 reaction\|S<sub>N</sub>1 reaction]], where the R<sub>1</sub> group initially dissociates from the phosphonium salt followed by attack of the anion.<ref name=":0" /> Halides that typically do not react in an S<sub>N</sub>2 or S<sub>N</sub>1-fashion, such as [[aryl]] halides, have been shown to participate in the Michaelis–Arbuzov reaction via free-radical mechanisms.<ref>{{Cite journal \|last1=Kostoudi \|first1=Stavroula \|last2=Pampalakis \|first2=Georgios \|date=2022-03-21 \|title=Improvements, Variations and Biomedical Applications of the Michaelis–Arbuzov Reaction \|journal=International Journal of Molecular Sciences \|language=en \|volume=23 \|issue=6 \|pages=3395 \|doi=10.3390/ijms23063395 \|doi-access=free \|issn=1422-0067 \|pmc=8955222 \|pmid=35328816}}</ref>

	Stereochemical experiments on cyclic phosphites have revealed the presence of both pentavalent [[phosphorane]]s and tetravalent phosphonium intermediates in [[chemical equilibrium]] being involved in the dealkylation step of the reaction using [[Phosphorus NMR\|<sup>31</sup>P NMR]]. The decomposition of these intermediates is driven primarily by the [[nucleophilicity]] of the anion. There exists many instances of the intermediate phosphonium salts being sufficiently stable that they can be isolated when the anion is weakly nucleophilic, such as with [[tetrafluoroborate]] or [[triflate]] anions.		Stereochemical experiments on cyclic phosphites have revealed the presence of both pentavalent [[phosphorane]]s and tetravalent phosphonium intermediates in [[chemical equilibrium]] being involved in the dealkylation step of the reaction using [[Phosphorus NMR\|<sup>31</sup>P NMR]]. The decomposition of these intermediates is driven primarily by the [[nucleophilicity]] of the anion. There exists many instances of the intermediate phosphonium salts being sufficiently stable that they can be isolated when the anion is weakly nucleophilic, such as with [[tetrafluoroborate]] or [[triflate]] anions.
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	In general, tertiary alkyl halides, aryl halides and vinyl halides do not react. There are notable exceptions to this trend, including [[1,2-dichloroethene]] and [[trityl]] halides. Some activated aryl halides, often involving [[Heterocyclic compound\|heterocycles]] have been known to undergo the reaction. [[Iodobenzene]] and substituted derivatives have been known to undergo the reaction under photolytic conditions. Secondary alkyl halides often do not react well, producing [[alkene]]s as side-products. Allyl and propargyl halides are also reactive, but can proceed through an S<sub>N</sub>2 or an S<sub>N</sub>2` mechanism. Reaction with primary alkyl halides and [[acyl halide]]s generally proceed smoothly. [[Carbon tetrachloride]] interestingly enough, only undergoes the reaction a single time with [[chloroform]] being inert to the reaction conditions. When a halide atom is found in the ester chain off of the phosphorus atom, [[isomerization]] to the corresponding Arbuzov product has been known without addition of an alkyl halide.		In general, tertiary alkyl halides, aryl halides and vinyl halides do not react. There are notable exceptions to this trend, including [[1,2-dichloroethene]] and [[trityl]] halides. Some activated aryl halides, often involving [[Heterocyclic compound\|heterocycles]] have been known to undergo the reaction. [[Iodobenzene]] and substituted derivatives have been known to undergo the reaction under photolytic conditions. Secondary alkyl halides often do not react well, producing [[alkene]]s as side-products. Allyl and propargyl halides are also reactive, but can proceed through an S<sub>N</sub>2 or an S<sub>N</sub>2` mechanism. Reaction with primary alkyl halides and [[acyl halide]]s generally proceed smoothly. [[Carbon tetrachloride]] interestingly enough, only undergoes the reaction a single time with [[chloroform]] being inert to the reaction conditions. When a halide atom is found in the ester chain off of the phosphorus atom, [[isomerization]] to the corresponding Arbuzov product has been known without addition of an alkyl halide.

	The [[Perkow reaction]] is a competing reaction pathway for α-bromo- and α-chloroketones. Under the reaction conditions a mixture of the Perkow product and the normal Arbuzov product occur, usually favoring the Perkow product by a significant amount. Using higher temperatures during the reaction can lead to favoring of the Arbuzov product. The reaction of α-iodoketones give only the Arbuzov product.<ref>{{cite journal \|author1=Jacobsen, H. I. \|author2=Griffin, M. J. \|author3=Preis, S. \|author4=Jensen, E. V. \| journal = [[J. Am. Chem. Soc.]] \| year = 1957 \| volume = 79 \| pages = 2608\| doi = 10.1021/ja01567a067\| title = Phosphonic Acids. IV. Preparation and Reactions of β-Ketophosphonate and Enol Phosphate Esters \| issue = 10}}</ref> Other methods of producing β-ketophosphonates have been developed.<ref>{{OrgSynth \| author = Nagata, W. \| author2 = Wakabayashi, T. \| author3 = Hayase, Y. \| collvol = 6 \| collvolpages = 448 \| year = 1988 \| prep = cv6p0448 \| title = Diethyl 2-(cyclohexylamino)vinylphosphonate}}</ref>		The [[Perkow reaction]] is a competing reaction pathway for α-bromo- and α-chloroketones. Under the reaction conditions a mixture of the Perkow product and the normal Arbuzov product occur, usually favoring the Perkow product by a significant amount. Using higher temperatures during the reaction can lead to favoring of the Arbuzov product. The reaction of α-iodoketones give only the Arbuzov product.<ref>{{cite journal \|author1=Jacobsen, H. I. \|author2=Griffin, M. J. \|author3=Preis, S. \|author4=Jensen, E. V. \| journal = [[J. Am. Chem. Soc.]] \| year = 1957 \| volume = 79 \| pages = 2608\| doi = 10.1021/ja01567a067\| title = Phosphonic Acids. IV. Preparation and Reactions of β-Ketophosphonate and Enol Phosphate Esters \| issue = 10\|bibcode=1957JAChS..79.2608J }}</ref> Other methods of producing β-ketophosphonates have been developed.<ref>{{OrgSynth \| author = Nagata, W. \| author2 = Wakabayashi, T. \| author3 = Hayase, Y. \| collvol = 6 \| collvolpages = 448 \| year = 1988 \| prep = cv6p0448 \| title = Diethyl 2-(cyclohexylamino)vinylphosphonate}}</ref>

	The reaction of trivalent phosphorus compounds with alkyl fluorides is abnormal. One example of this reactivity is shown below.		The reaction of trivalent phosphorus compounds with alkyl fluorides is abnormal. One example of this reactivity is shown below.

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Alkyl halide: move ref out of heading

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{{Short description|Chemical reaction}}
{{Reactionbox
| Name = Michaelis–Arbuzov reaction
| Type = Coupling reaction
| NamedAfter = [[August Michaelis]] [[Aleksandr Arbuzov]]
| Section3 = {{Reactionbox Identifiers
| OrganicChemistryNamed = arbuzov-reaction
| RSC_ontology_id = 0000060
}}
}}
The '''Michaelis–Arbuzov reaction''' (also called the '''Arbuzov reaction''') is the [[chemical reaction]] of a [[trivalent]] phosphorus ester with an [[alkyl halide]] to form a [[pentavalent]] phosphorus species and another alkyl halide. The picture below shows the most common types of substrates undergoing the Arbuzov reaction; [[phosphite ester]]s ('''1''') react to form [[phosphonate]]s ('''2'''), [[phosphonite]]s ('''3''') react to form [[phosphinate]]s ('''4''') and [[phosphinite]]s ('''5''') react to form [[phosphine oxide]]s ('''6''').
[[File:Arbuzov_Reaction_Scope.png|alt=|center|401x401px]]
The reaction was discovered by [[August Michaelis]] in 1898,<ref>{{cite journal |author1=Michaelis, A. |author2=Kaehne, R. | journal = [[Berichte]] | year = 1898 | volume = 31 | pages = 1048–1055 | title = Ueber das Verhalten der Jodalkyle gegen die sogen. Phosphorigsäureester oder O-Phosphine| doi = 10.1002/cber.189803101190|url=https://zenodo.org/record/1425896}}</ref> and greatly explored by [[Aleksandr Arbuzov]] soon thereafter.<ref>{{cite journal | author = Arbuzov, A. E. | journal = J. Russ. Phys. Chem. Soc. | year = 1906 |title=On the structure of phosphonic acid and its derivates: Isometization and transition of bonds from trivalent to pentavalent phosphorus. | volume = 38 | pages = 687}}</ref><ref>{{cite journal | author = Arbuzov, A. E. | journal = Chem. Zentr. | year = 1906 | volume = II | pages = 1639}}</ref> This reaction is widely used for the synthesis of various phosphonates, [[phosphinate]]s, and [[phosphine oxide]]s. Several reviews have been published.<ref>{{cite journal | author = Arbuzov, B. A. | journal = [[Pure Appl. Chem.]] | year = 1964 | volume = 9 | pages = 307–353 | doi = 10.1351/pac196409020307 | title = Michaelis–Arbusow- und Perkow-Reaktionen | issue = 2 | s2cid = 93719226 | doi-access = free }}</ref><ref name=":0">{{cite journal |author1=Bhattacharya, A. K. |author2=Thyagarajan, G. | journal = [[Chem. Rev.]] | year = 1981 | volume = 81 | pages = 415–430 | title = Michaelis–Arbuzov rearrangement | doi = 10.1021/cr00044a004 | issue = 4}}</ref> The reaction also occurs for coordinated phosphite ligands, as illustrated by the demethylation of {(C5H5)Co[(CH3O)3P]3}2+ to give {(C5H5)Co[(CH3O)2PO]3}−, which is called the [[Klaui ligand]].

==Reaction mechanism==
[[file:Michaelis-Arbuzov Reaction Mechanism.png|center|600px|The mechanism of the Michaelis–Arbuzov reaction]]

The Michaelis–Arbuzov reaction is initiated with the [[SN2 reaction|SN2 attack]] of the [[nucleophilic]] phosphorus species ('''1''' - A phosphite) with the [[electrophilic]] alkyl halide ('''2''') to give a [[phosphonium salt]] as an intermediate ('''3'''). These intermediates are occasionally stable enough to be isolated, such as for triaryl phosphites which do not react to form the phosphonate without thermal cleavage of the intermediate (200 °C), or cleavage by alcohols or bases. The displaced [[halide]] anion then usually reacts via another SN2 reaction on one of the R1 carbons, displacing the oxygen atom to give the desired phosphonate ('''4''') and another alkyl halide ('''5'''). This has been supported by the observation that chiral R1 groups experience inversion of configuration at the carbon center attacked by the halide anion. This is what is expected of an SN2 reaction.<ref>{{cite journal |author1=Gerrard, W. |author2=Green, W. J. | journal = J. Chem. Soc. | year = 1951 | pages = 2550| doi = 10.1039/jr9510002550| title = 568. Mechanism of the formation of dialkyl alkylphosphonates}}</ref> Evidence also exists for a [[carbocation]] based mechanism of dealkylation similar to an [[SN1 reaction|SN1 reaction]], where the R1 group initially dissociates from the phosphonium salt followed by attack of the anion.<ref name=":0" /> Phosphite esters with tertiary alkyl halide groups can undergo the reaction, which would be unexpected if only an SN2 mechanism was operating. Further support for this SN1 type mechanism comes from the use of the Arbuzov reaction in the synthesis of [[neopentyl]] halides, a class of compounds that are notoriously unreactive towards SN2 reactions. Based on the principle of [[microscopic reversibility]], the inert nature of the neopentyl halides towards the SN2 reaction indicates that an SN2 reaction is unlikely to be the mechanism for the synthesis of the neopentyl halides in this reaction. Substrates that cannot react through an SN2 pathway or an SN1 pathway generally do not react, which include [[vinyl group|vinyl]] and [[aryl]] groups. For example, the triaryl phosphites mentioned above generally do not react because they form stable phosphonium salts. Since aryl groups do not undergo SN1 and SN2 type mechanisms, triaryl phosphites lack a low energy pathway for decomposition of the phosphonium salt. An [[allylic rearrangement]] mechanism ('''SN2'''') has also been implicated in [[Allyl group|allyl]] and [[propargyl]] halides.

Stereochemical experiments on cyclic phosphites have revealed the presence of both pentavalent [[phosphorane]]s and tetravalent phosphonium intermediates in [[chemical equilibrium]] being involved in the dealkylation step of the reaction using [[Phosphorus NMR|31P NMR]]. The decomposition of these intermediates is driven primarily by the [[nucleophilicity]] of the anion. There exists many instances of the intermediate phosphonium salts being sufficiently stable that they can be isolated when the anion is weakly nucleophilic, such as with [[tetrafluoroborate]] or [[triflate]] anions.

== Scope ==

=== Alkyl halide ===
Source:<ref name=":0" />

As a general guideline, the reactivity of the organic halide component can be listed as follows: (from most reactive to least reactive)

:<chem>RCOX > RCH2X > RR'CHX \gg RR'R''CX</chem>

and

:<chem>RI > RBr > RCl</chem>

In general, tertiary alkyl halides, aryl halides and vinyl halides do not react. There are notable exceptions to this trend, including [[1,2-dichloroethene]] and [[trityl]] halides. Some activated aryl halides, often involving [[Heterocyclic compound|heterocycles]] have been known to undergo the reaction. [[Iodobenzene]] and substituted derivatives have been known to undergo the reaction under photolytic conditions. Secondary alkyl halides often do not react well, producing [[alkene]]s as side-products. Allyl and propargyl halides are also reactive, but can proceed through an SN2 or an SN2` mechanism. Reaction with primary alkyl halides and [[acyl halide]]s generally proceed smoothly. [[Carbon tetrachloride]] interestingly enough, only undergoes the reaction a single time with [[chloroform]] being inert to the reaction conditions. When a halide atom is found in the ester chain off of the phosphorus atom, [[isomerization]] to the corresponding Arbuzov product has been known without addition of an alkyl halide.

The [[Perkow reaction]] is a competing reaction pathway for α-bromo- and α-chloroketones. Under the reaction conditions a mixture of the Perkow product and the normal Arbuzov product occur, usually favoring the Perkow product by a significant amount. Using higher temperatures during the reaction can lead to favoring of the Arbuzov product. The reaction of α-iodoketones give only the Arbuzov product.<ref>{{cite journal |author1=Jacobsen, H. I. |author2=Griffin, M. J. |author3=Preis, S. |author4=Jensen, E. V. | journal = [[J. Am. Chem. Soc.]] | year = 1957 | volume = 79 | pages = 2608| doi = 10.1021/ja01567a067| title = Phosphonic Acids. IV. Preparation and Reactions of β-Ketophosphonate and Enol Phosphate Esters | issue = 10}}</ref> Other methods of producing β-ketophosphonates have been developed.<ref>{{OrgSynth | author = Nagata, W. | author2 = Wakabayashi, T. | author3 = Hayase, Y. | collvol = 6 | collvolpages = 448 | year = 1988 | prep = cv6p0448 | title = Diethyl 2-(cyclohexylamino)vinylphosphonate}}</ref>

The reaction of trivalent phosphorus compounds with alkyl fluorides is abnormal. One example of this reactivity is shown below.
[[File:Arbuzov_Scope_Fluorine_Reactivity.png|center|400x400px]]

=== Phosphorus reactant ===
The general form of the trivalent phosphorus reagent can be considered as follows: <chem>ABP-OR</chem> with A and B generally being alkyl, alkoxy or aryloxy groups. [[Electron-withdrawing]] groups are known to slow down the rate of the reaction, with electron donating groups increasing the rate of the reaction. This is consistent with initial attack of the phosphorus reagent on the alkyl halide as the [[rate-determining step]] of the reaction. The reaction proceeds smoothly when the R group is aliphatic. When all of A, B and R are aryl groups, a stable phosphonium salt is formed and the reaction proceeds no further under normal conditions. Heating to higher temperatures in the presence of alcohols has been known to give the isomerization product. Cyclic phosphites generally react to eject the non-cyclic OR group, though for some 5-member rings additional heating is required to afford the final cyclic product.<ref name=":0" />
[[File:Arbuzov_Scope_Cyclic_Phosphite.png|alt=|center|446x446px]]
Phosphite salts (Ex: R = Na) can also undergo the reaction with precipitation of the corresponding Na-halide salt. Amidophosphites and silyloxyphosphites have been used before to yield amidophosphonates and phosphinic acids.<ref name=":0" />
[[File:Arbuzov_Scope_Silylmethoxy.png|alt=|center|424x424px]]
An Arbuzov type rearrangement can also occur where the O from an OR group acts as the leaving group in the initial SN2 attack of the phosphorus. This is only known to occur when A and B are Cl.<ref name=":0" />
[[File:Arbuzov_scope_PCl3_rearrangement.svg|center|228x228px]]

Phosphite esters are the least reactive class of reagents used in this reaction. They react to produce phosphonates. They require the most heating for the reaction to occur (120 °C - 160 °C is common). This high temperature allows for fractional distillation to be employed in the removal of the alkyl halide produced, though excess of the starting alkyl halide can also be used. Solvents are often not used for this reaction, though there is precedent for the improvement of selectivity with its usage.<ref name=":0" />

Phosphonites are generally more reactive than phosphite esters. They react to produce phosphinates. Heating is also required for the reaction, but [[pyrolysis]] of the ester to an acid is a common side reaction. The poor availability of substituted phosphonites limits the usage of this class of reagent in the Arbuzov reaction. [[Hydroxy group|Hydroxy]], [[thiol]], [[carboxylic acid]], primary and secondary [[amine]] functional groups cannot be used with phosphonites in the reaction as they all react with the phosphonite.<ref name=":0" />

Phosphinites are the most reactive class of reagents used in this reaction. They react to produce phosphine oxides. They often require very little heating (45 °C) for the reaction to occur and have been known to self-isomerize without the presence of alkyl halides.<ref name=":0" />

The Arbuzov rearrangement generally does not admit a thiologous analogue, except when the phosphorus is substituted with strongly electron-donating groups.<ref>{{cite book|title=Sulfur in Organic and Inorganic Chemistry|volume=1|editor-first=Alexander|editor-last=Senning|year=1971|publisher=Marcel Dekker|location=New York|lccn=70-154612|isbn=0-8247-1615-9|first=Lucreţia|last=Almasi|chapter=The Sulfur–Phosphorus Bond|pages=51–55|postscript=,}} although note that Almasi identifies the chemoselective axis as [[HSAB|hard-softness]] instead.</ref>

==See also==
*[[Abramov reaction]]
*[[Perkow reaction]]
*[[Michaelis–Becker reaction]]
*[[Hirao coupling]]

==References==
{{Reflist}}

==External links==
* Ford-Moore, A. H.; Perry, B. J. ''Organic Syntheses'', Coll. Vol. 4, p. 325 (1963); Vol. 31, p. 33 (1951). ([https://web.archive.org/web/20120716191608/http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0325 Article])
* Davidsen, S. K.; Phllips, G. W.; Martin, S. F. ''Organic Syntheses'', Coll. Vol. 8, p. 451 (1993); Vol. 65, p. 119 (1987). ([https://web.archive.org/web/20120716191612/http://www.orgsyn.org/orgsyn/prep.asp?prep=cv8p0451 Article])
* Enders, D.; von Berg, S.; Jandeleit, B. ''Organic Syntheses'', Coll. Vol. 10, p. 289 (2004); Vol. 78, p. 169 (2002). ([https://web.archive.org/web/20120716191616/http://www.orgsyn.org/orgsyn/prep.asp?prep=v78p0169 Article])
{{Organic reactions}}
{{DEFAULTSORT:Michaelis-Arbuzov reaction}}
[[Category:Substitution reactions]]
[[Category:Name reactions]]