Skipped diynes. V. Secondary diethynyl carbinols. Base-catalyzed ynol to enol rearrangements and ultraviolet spectra and conjugation

KG Migliorese, Y Tanaka, SI Miller

文献索引：Migliorese,K.G. et al. Journal of Organic Chemistry, 1974 , vol. 39, p. 739 - 747

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被引用次数: 24

摘要

Bis (1-propyny1) methanol (la), bis (phenylethyny1) methanol (lb), and tetrakis (l-propynyl) cthane-l, 2-diol (10) are highly activated propargyl alcohols. Because of their sensitivity to acid, conversions of 1 to carbamate, ester, ether, and halide best proceed under neutral or basic conditions. Even so, disruptions of the diyne system are common, eg, the formation of 4-bromo-2, 5-heptadiyne and 2-bromo-2, 3-heptadien-5-yne from la, thermal cleavage of ...