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Face Selectivity of the Diels-Alder Additions of 2-Substituted 5,6-bis((E)-chloromethylidene)bicyclo[2.2.2]octanes

✍ Scribed by Marco Avenati; Pierre Vogel

Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
815 KB
Volume
65
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The preparation of 5,6‐bis((E)‐chlorommethylidene)bicyclo[2.2.2]oct‐2‐ene (13), 2,3‐bis((E)‐chloromethyl idene)‐5__exo,6exo__‐ and ‐5__endo,6endo__‐epoxybicyclo[2.2.2] octane (14 and 15), 5,6‐bis((E)‐chloromethylidene)‐2__exo__‐ and ‐2__endo__‐bicyclo[2.2.2] octanol (16 and 17) and 5,6‐bis((E)‐chloromethylidene)‐2‐bicyclo[2.2.2]octanone (18) are described. The face selectivity (endo‐face vs. exo‐face attack onto the exo‐cyclic diene) of their cycloadditions to tetracyanoethylene has been determined in benzene at 20°. It is 78/22, 80/20, 60/40, 68/32, 3/97 and 30/70 for 13, 14, 15, 16, 17 and 18, respectively.

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