Tetrahedron

Additions of carbenium ions to nonconjugated dienes. The retarding (− I)-effect of the second double bond.

B Irrgang, H Mayr

Index: Irrgang,B.; Mayr,H. Tetrahedron, 1991 , vol. 47, p. 219

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Citation Number: 11

Abstract

Kinetics for the addition of the p-methoxybenzhydryl cation (AnPhCH+, 10) towards nonconjugated dienes 11 [H2C= C (CH3)-(CH2) nC (CH3)= CH2] have been determined in CH2Cl2 at− 30° to− 70° C. Reactivity increases with increasing number of methylene groups separating the two double bonds. For n= 4, reactivity reaches the value for saturated alkyl substituents, and nucleophilic assistance of the second double bond is never observed.