ISSN:
0009-2940
Keywords:
Elimination
;
Hydride shift
;
Spirocyclization
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Transannular Hydride Shift versus Cyclocondensation in 5-(2-Biphenylyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol DerivativesThe title compounds 1a-c, stable under thermal and basic conditions, undergo a solvent-assisted concerted hydride shift/deprotonation reaction to 5-(2-biphenylyl)-5H-dibenzo[a,d]cycloheptene (4) in weak acids such as acetic acid, acetic anhydride, phenol, and nitromethane. In strong acids like formic acid or trifluoroacetic acid cyclization to 10,11-dihydrospiro[5H-dibenzo[a,d]cycloheptene-5,9′-fluorene] (3) occurs via the carbenium ion intermediate 5.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19891220832
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