Radical ion probes. 11. Reaction of 1,1-dimethyl-5,7-di-t-butylspiro[2.5]octa-4,7-dien-6-one with 5-hexenyl magnesium bromide

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• 作者：Gillmore ; Jason G. ; Tanko ; James M.
• 刊名：Tetrahedron Letters
• 出版年：1998
• 出版时间：November 26, 1998
• 年：1998
• 卷：39
• 期：48
• 页码：8795-8798
• 全文大小：211 K

文摘

In an ongoing effort to establish 1,1-dimethyl-5,7-di-t-butylspiro[2.5]octa-4,7-dien-6-one (1) as a mechanistic probe for the detection of single electron transfer (SET), the reaction of 1 with 5-hexenyl magnesium bromide was examined in the hopes of observing cyclization of any intermediate 5-hexenyl radicals to cyclopentylcarbinyl radicals. A polar process dominated the reaction, but in the less prevalent SET process, the 5-hexenyl → cyclopentylcarbinyl rearrangement was extensive, indicative of freely diffusing paramagnetic intermediates.