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Evaluation of the π-conjugative effect of the 2-methylene and the 2-oxo substituent on the stability of carbocations in the solvolysis of bicyclic bridgehead derivatives

✍ Scribed by Ken'ichi Takeuchi; Fumio Akiyama; Keizo Ikai; Tadashi Shibata; Midori Kato

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
280 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

The cyano and carbonyl groups are strongly electron withdrawing (-I). However. in recent years considerable experimental and theoretical efforts have been made in evaluating the ITconjugative electron donation (+M) of these substituents toward cationic carbon (schemes 1 and 2).' As for the effect of the cyano substituent. solvolytic studies have been successfully applied, suggesting the conjugative nature between the cyano moiety and the cationic center (scheme l).la*b

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