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Chemistry of Isodrin Derivatives. The Syntheses of 11‐ and 12‐Hydroxy‐1,4,4a,9,9a,10‐Hexahydro‐ Endo, Endo ‐1,4;9,10‐Dimethano‐Anthracenes
Author(s) -
Chow Tahsin J.
Publication year - 1996
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199600016
Subject(s) - chemistry , cyclopentadiene , aromatization , moiety , methylene , norbornadiene , medicinal chemistry , double bond , stereochemistry , organic chemistry , catalysis
The titled compounds are synthesized through multi‐step sequences involving consecutive [ n 4 s + n 2 s ] cycloadditions of norbornadiene with two units of chlorinated cyclopentadiene. A dyotropic double hydrogen migration was observed between two closely located double bonds during the process of aromatization of a cyclohexadiene moiety. A hydroxyl group is introduced onto either of the two methylene bridges in order to provide products suitable for solvolytic analyses.