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Reaction of thioxophosphorane sulfenyl bromides with ethyl vinyl ether: Mechanistic and synthetic aspects

✍ Scribed by Marek J. Potrzebowski; Andrzej Łopusiński; Jan Michalski

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
524 KB
Volume
2
Category
Article
ISSN
1042-7163

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✦ Synopsis

The mechanistic and synthetic aspects o f the addition reaction of thioxophosphorane sulfenyl bromide with ethyl vinyl ether were studied in detail by N M R techniques. It has been found that the regiospecific, primary product of the reaction, I -bromo-1-ethoxy-2S(dialkoxythiophosphoryl)ethane I , is unstable and undergoes slow decomposition to give four compounds. The formation of thiophosphoryl derivatives, vinyl ethers I I and III, aldehyde IV, and the symmetrical hemiacetal anhydride V , has been considered in terms of a carbocation intermediate. By choice of the appropriate reaction conditions, the aldehyde IV can be obtained in very high yield.

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