Additions of trialkyl phosphites to nitroalkenes

WE Krueger, MB McLean, A Rizwaniuk…

Index: Krueger,W.E. et al. Journal of Organic Chemistry, 1978 , vol. 43, p. 2877 - 2879

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Citation Number: 13

Abstract

The reaction of d-nitrostyrene (1) with triethyl phosphite in DME gave diethyl a- styrylphosphonate (2b) in 85% yield. In DME/lO% HZ0 it gave a 5050 mixture of 2b and 1- diethoxyphosphinyl-1-phenyl-2-nitroethane(5b). In DME/lO% D20 with trimethyl phosphite it gave products with deuterium incorporated in the position 6 to the phenyl group in both 2a and 5a. Mechanistic implications are discussed.