Abstract
Methylidynephosphane ( 2) is generated under flash pyrolytic conditions by cleavage of isobutene from the phosphaalkyne ( 1) or by elimination of hydrogen chloride from dichloromethylphosphine ( 3). It undergoes [3 + 2]-cycloaddition reactions with stable dipoles eq. diazo compounds ( 2 + 4a,b → 5a,b), methyl azide ( 2 + 7 → 8), benzonitriloxide ( 2 + 10 → 12, 1:2-adduct) and 3-methyl-2,4-diphenyl-1,3-oxazolium-5-olate ( 2 + 13 → 15) to give the corresponding phospholes. Silylated phosphaalkene ( 19) can be used as a synthetic substitute for 2: the 5-trimethylsilyl-1 H-1,2,4-diazaphospholes ( 22), which result from the reaction of 19 and the diazo compounds 4 with chlorotrimethylsilane elimination, are desilylated to 5 by potassium fluoride in dimethyl formamide.
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