Other Reactions and Properties of Olefins

Other Reactions and Properties of Olefins.— The addition products of 4-chlorobenzenesulphenyl chloride with a number of cyclic and acyclic olefins, e.p. (373), exchange 4-chlorobenzenesulphenyl chloride with oct-l-ene when 

Reaction of iV-bromoacetamide (NBA) with olefins leads to the unknown 2-bromo-AT-bromoacetimidates (375), The first stage is a radical reaction of NBA with itself to give (376), followed by ionic addition of the latter to the double bond. 

Dunogues, and M. Bolourtchian, /. Organometallic Chem 1971, 26,195. W. Fink, Helv. Chim. Acta, 1971, 54, 1304. 

The cycloalkene trifluoromethanesulphonates (inflates) have been used to generate the bent vinyl cations whose preferred geometry is calculated to be linear. In agreement, the solvolysis rates of cyclic Inflates decrease with decreasing ring size. The products are exclusively cycloalkanones when water is present, e.g. (380) - (381).  

An A -ray crystallographic study of an acetate (382) derived from katonic acid shows it to have a twisted double bond with angles as shown (383). This severe twisting helps to explain the u.v. spectrum of the derived C29 alcohol which has Ajjj 229 nm (e 5180) in ethanol.  

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