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Mesomeric Vinyl Cations. Part III. Stereochemistry of cations derived from 2‐bromo‐1, 3‐dienes
Author(s) -
Grob C. A.,
Pfaendler H. R.
Publication year - 1970
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.19700530825
Subject(s) - chemistry , steric effects , solvolysis , diene , double bond , medicinal chemistry , ion , stereochemistry , bent molecular geometry , organic chemistry , hydrolysis , natural rubber
In contrast to their acyclic analogues, 2‐bromocyclohexa‐1, 3‐diene ( 11a ) and 3‐bromo‐1, 5‐dimethyl‐cyclohexa‐1, 3‐diene ( 11b ) do not react with silver ion, nor do they undergo solvolysis in 80% ethanol at temperatures up to 180°. The inertness to ionization of these cyclic bromodienes is attributed to steric inhibition of mesomerism involving the π electrons of the second double bond in the planar vinyl cation 12 and to the bent structure of this hypothetical intermediate.