Solvolysis of syn-endo-tricyclo[3,2,1,02,4]oct-6-en-8-yl p-nitrobenzoate

Abstract

The rates of solvolysis of the title compound in 70% 1,4-dioxan–water were measured at 150, 160, and 170°. At the highest temperature, this material reacts ten times faster than anti-norbornen-7-yl p-nitrobenzoate. The products of solvolysis in either buffered or unbuffered dioxan–water were examined after six half-lives. Over 90% of the product mixture consists of the alcohol that corresponds to starting material. This result shows that the source of cationic stabilization does not shift during the reaction from the double bond to the cyclopropane ring.