The reaction of lithium trialkylalkynylborate with methanesulphinyl chloride. A novel route to internal acetylenes
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説明
Abstract Treatment of lithium trialkylalkynylborates (1) with methanesulphinyl chloride gives internal acetylenes (2) in good yields. The reaction proceeds via β-methanesulphinylvinylboranes 3, followed by cis elimination of methanesulphinyl group and dialkylboron groups. The reaction mixture of B-alkyl-9-BBN and 1-lithio-1-heptyne has been treated with methanesulphinyl chloride to provide mainly a cyclooctane derivative 6. This finding is explained in terms of the steric factors in the approach of the methanesulphinyl chloride.
収録刊行物
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- Tetrahedron Letters
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Tetrahedron Letters 14 1847-1850, 1973-01-01
Elsevier BV