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Paper | Regular issue | Vol 48, No. 9, 1998, pp.1903-1915
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8226
Reaction of (Vinylimino)phosphoranes with Electron-deficient Acetylenes: Synthesis and Reactivity of 1,2λ5-Azaphosphinines

Hiroyuki Yamamoto, Tomoshige Kobayashi, and Makoto Nitta*

*Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan


The reactions of trimethoxy(1-Phenylvinylimino)phosphorane and methoxydiphenyl(1-phenylvinylimino)phosphorane with electrone-deficient acetylenes results in the formation of 1,2-λ5-azaphosphinines (7a,b) and (9a,b), while those of triphenyl(1-phenylvinylimino)phosphorane and trimethoxy(vinylimino)phosphorane with dimethyl acetylenedicarboxylate (DMAD) proceeds via formal [2+2] cycloadducts to give functionalized butadienes. Thermal rearrangement of 7a,b and the preparation of HBF4 salts of 9a,b are studied. Reactions of compounds 7a,b and 9a with DMAD leading to λ5-phosphinine derivatives are studied as well.