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Bridged Annulenes
Author(s) -
Vogel Emanuel
Publication year - 1980
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.198000075
Subject(s) - annulene , chemistry , ring (chemistry) , acene , aromaticity , synthon , stereochemistry , steric effects , series (stratigraphy) , computational chemistry , molecule , organic chemistry , paleontology , biology
The synthesis and aromaticity of 1,6‐methano[10]annulene and its analogues containing a heteroatom bridge suggested the possibility that the homologous series of bridged [4 n + 2]annulenes 1, 2, 3 , etc., formally derived from the acene series, could be developed. In the pursuit of this concept a set of systematically bent bridged [14]annulenes which permitted a scrutinization of the steric prerequisite of the Hückel rule — the requirement of a planar ring skeleton — were built up. Moreover, a new synthetic strategy based on the synthon cycloheptatriene‐1,6‐dicarboxaldehyde has provided access to the two next higher homologues (syn‐series) of 1,6‐methano[10]annulene, i.e., syn‐1,6:8,13‐bismethano[14]annulene and syn, syn‐1,6:8,17:10,15‐trismethano[18]annulene, respectively.