期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 4, 页码 1451-1462出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo302524a
关键词
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The Diels-Alder (DA) reaction channel of the thermal C-2-C-6 (Schmittel) cyclization of enyne-allenes is studied computationally and experimentally evaluating the influence of temperature on product ratios. Remote substituents at the alkyne terminus influence the mechanism of the C-2-C-6/DA cyclization steering it either to a stepwise or a concerted course. Temperature independent product ratios, selectivity of product formation, and computational results obtained at (U)BLYP/6-31G(d) level unveil a mechanism that is strongly controlled by nonstatistical dynamics.
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