Reactions of Alkyl Diphenylphosphinates and Related Thio Esters with Some Nucleophiles. SN 2 (S) Reaction and Wittig Type Rearrangement

K Goda, R Okazaki, K Akiba, N Inamoto

Index: Goda,K. et al. Bulletin of the Chemical Society of Japan, 1978 , vol. 51, p. 260 - 264

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Citation Number: 18

Abstract

Reactions of alkyl diphenylphosphinates Ph 2 P (= X) YCHR 1 R 2 (X, Y= O, S) with organolithiums and Grignard reagents afforded different types of products depending on the combination of X and Y. When Y= O, the reagents (R 3 M) mainly attacked the phosphorus atom to give Ph 2 P (= X) R 3 and R 1 R 2 XCHO− irrespective of X, while, when X= Y= S, the reaction occurred exclusively at the ester sulfur atom, SN 2 (S), to give R 3 SCHR 1 R 2 ...