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Primary dependence of 7-aryl-2,5-di-t-butyl-1,3,5-cycloheptatriene valence tautomerism on the π-acceptor strength of the 7-aryl substituent

✍ Scribed by Ken'ichi Takeuchi; Hiroshi Fujimoto; Kunio Okamoto

Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 245 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)92397-4

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✦ Synopsis

l3 C NMR studies showed that the population of the norcaradiene form of the title systems containing p-CH30, H, and p-CF3 on the 7-aryl group increases in this order. The result is consistent with the prediction from the n-acceptor strength of the aryl group estimated by INDO calculations.

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Singlet oxygenation of 7-aryl and 7-alkyl-1,3,5-cycloheptatrienes: substituent effects on the product distribution of tropilidene- and nocaradiene-derived endoperoxides

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The N/T ratio, 1. e. the proportion of norcaradlene (u) versus tropilldene (1) endopero xldes in the cycloaddltlon of singlet oxygen with 7-substituted 1,3,5-cycloheptatrlenes, decreases in the order p-C1C6H4 > C6H5 >p-MeOC6H4 and t-Bu > l-Pr > Et > Me, presumably reflecting the ability of these sub