SPECIFIC REACTIONS OF CYANOALKYLSULFUR CO MPOUNDS - APPLICATION TO SYNTHESIS OF ACRYLIC DERIVATIVES

The reactivity of Ph-SH with acrylic compounds permits a protection of the acrylic double bond and reaction on the protected product. In som e cases (cyano alkyl acrylic compounds) a specific reaction can be obs erved. So action of KCN on PhS-(CH2)(2)-COO-(CH2)(n)Cl [n = 2,3] gives NC-(CH2)(2)-COO-(CH2)(n)SPh [the expected compound (PhS-(CH2)(2)-COO- (CH2)(n)CN) was not isolated]. We involve a sulfonium ion as intermedi ate for this ''abnormal'' reaction. When n = 6 the normal protection/d eprotection reaction occurs.