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

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

Author(s) -

Avenati Marco,

Vogel Pierre

Publication year - 1982

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19820650119

Subject(s) - chemistry , bicyclic molecule , tetracyanoethylene , selectivity , octane , bridged compounds , medicinal chemistry , octene , stereochemistry , organic chemistry , ethylene , catalysis

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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