RING-OPENING REACTIONS OF SOME PHOSPHORYL-SUBSTITUTED CYCLOPROPANES BY -NH AND -SH NUCLEOPHILES

Reactions of (1-cyanocyclopropyl)diphenylphosphine oxide (1a) with -NH and -SH nucleophiles gave the anticipated ring-opened products, while those of (1-ethoxycarbonylcyclopropyl)diphenylphosphine oxide (1b) or diethyl 1-cyano- and 1-ethoxycarbonylcyclopropylphosphonates (1c-d) w ere often deflected by ester-exchange reactions. The ring-opened produ cts of la by amines reacted with aromatic aldehydes under PTC conditio ns to produce homoallylic amines in good yields. (C) 1996 John Wiley & Sons, Inc.