or<\/p>\n\n\n\n
https:\/\/www.csulb.edu\/chemistry-biochemistry\/page\/jeffrey-cohlberg-phd<\/a><\/p>\n\n\n\n <\/p>\n\n\n\n The Michaelis-Arbuzov reaction is initiated with the SN2 reaction of the nucleophilic phosphite with the electrophilic alkyl halide to give a phosphonium intermediate. Triaryl phosphites, which are unable to perform the second step of the Michaelis-Arbuzov reaction, have been shown to produce stable phosphonium salts.Likewise, aryl and vinyl halides are unreactive towards phosphites.<\/p>\n\n\n\n The displaced halide anion reacts via another SN2 reaction with the phosphonium intermediate to give the desired phosphonate and another alkyl halide.<\/p>\n\n\n\n When chiral phosphonium intermediates are produced, it has been shown the halide substitution proceeds with inversion of configuration, as expected by a SN2 reaction.<\/p>\n\n\n\n I used to understand this…. not anymore…<\/i><\/p>\n\n\n\n Updated 2025<\/a>, thanks Jeff<\/p>\n\n\n\n <\/p>\n","protected":false},"excerpt":{"rendered":" The Biochemists Songbook MP3 Files has a new home http:\/\/www.csulb.edu\/~cohlberg\/songbook.html https:\/\/sites.google.com\/view\/biochemists-songbook or https:\/\/www.csulb.edu\/chemistry-biochemistry\/page\/jeffrey-cohlberg-phd The Michaelis-Arbuzov reaction is initiated with the SN2 reaction of the nucleophilic phosphite with the electrophilic alkyl halide to give a phosphonium intermediate. Triaryl phosphites, which are … Continue reading ![\"Michaelis](\"http:\/\/i491.photobucket.com\/albums\/rr277\/Nolligan\/600px-Michaelis-Arbuzov_Reaction_Me.png\")
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