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Communication | Regular issue | Vol 22, No. 6, 1984, pp.1331-1334
Published online, 1st January, 1970
DOI: 10.3987/R-1984-06-1331
Reductive Formation of Pyrimidinylmethylenephosphoranes by Reaction of Trichloromethylpyrimidines with Triphenylphosphine

Shoetsu Konno, Yumi Sato, Takao Sakamoto, Nobuya Katagiri, and Hiroshi Yamanaka*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

The reaction of trichloromethylpyrimidines (1) with ca. 5 equivalent amounts of TPP gave pyrimidinylmethylenephosphoranes (9), whereas in the presence of 2 equivalent amounts of TPP, 1 was converted into the corresponding pyrimidinylchloromethylenephosphosphoranes (2). Condensation of 2 and 9 with aldehydes gave smoothly pyrimidine derivatives having an olefinic side chain. The pathway of the reduction to form the phosphoranes was discussed with experimental evidence.