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Title: Azaborine benzylic ion stability and reactivity in ionic polymerization
Benzylic cations and anions are implicated in the mechanism of critical organic transformations, such as styrene polymerization. We investigate the influence of BN for CC bond substitution on the reactivity of benzylic ions and the effect on BN 2-vinylnaphthalene (BN2VN) ionic polymerization. Calculations suggest that the proximity of a N donor to a cation influences the stability of a BN benzylic cation, rationalizing unsuccessful protonation of BN2VN. Organolithium reagents undergo clean nucleophilic aromatic substitution with BN2VN and related BN naphthalenes via a hypothesized associative mechanism. These results suggest design principles for main group aromatic substitution.  more » « less
Award ID(s):
1752791
PAR ID:
10402052
Author(s) / Creator(s):
; ;
Date Published:
Journal Name:
Organic & Biomolecular Chemistry
Volume:
20
Issue:
7
ISSN:
1477-0520
Page Range / eLocation ID:
1407 to 1414
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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