Author:
Carter Jennifer,Fenwick Michael H,Huang Wen-wei,Popik Vladimir V,Tidwell Thomas T
Abstract
1-Naphthylketene (2), generated by thermal Wolff-rearrangement, is trapped in situ by 2,2,6,6-tetramethylpiridinyloxy radical (TEMPO, TO·) to form the adduct 1-naphthCH(OT)CO2T (4), whose structure is confirmed by an X-ray determination. The 1H NMR spectrum of 4 displays three CH3 groups with very high field chemical shifts (δ 0.10-0.47), and this is attributed to the location of these groups in the shielding region above the π system of the naphthyl ring. At -40°C, doubling of most of the 1H NMR signals occurs, and this is attributed to a freezing out of two conformations differing by rotation around the naphthylCH bond.Key words: ketene, TEMPO, restricted rotation, 1H NMR, conformational analysis, free radicals.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
11 articles.
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