Regioselective Lithium–Iodine Exchange-Initiated Cleavage of 2-Iodomethyl-1,3-dioxanes: A Complex-Induced Proximity Effect

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• 作者：William F. Bailey ; Justin D. Fair
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：81
• 期：9
• 页码：3951-3955
• 全文大小：273K
• 年卷期：0
• ISSN：1520-6904

文摘

Lithium–iodine exchange-initiated fragmentation of a series of 4-substituted 2-iodomethyl-1,3-dioxanes proceeds rapidly and regioselectively to afford enol ether alcohols by preferential cleavage of the less congested C(2)–O(1) bond. The results demonstrate that a complex-induced proximity effect (CIPE) is likely responsible for the selectivity of the cleavage.