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1,2‐Bridged Quadricyclanes
Author(s) -
Hart Harold,
Peng ChengTai
Publication year - 1982
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198200009
Subject(s) - norbornadiene , chemistry , quadricyclane , acetylene , ring (chemistry) , catalysis , polymer chemistry , medicinal chemistry , stereochemistry , organic chemistry
The readily available benzodihydropentalene 6 and dimethyl acetylene‐dicarboxylate react to give norbornadiene diester 8 , with a three‐carbon bridge from C 1 to C 2 . Inrradiation of 8 gives the corresponding C 1 ‐C 2 bridged quadricyclane diester 9 , a new ring system. Diester 9 is quite stable, reverting to 8 with a t 1/2 of 30 min at 170°C. The corresponding diacid 11 , also prepared, reverts to its norbornadiene precursor at a considerably lower temperature, possibly as a consequence of acid catalysis.