An Efficient Synthesis of Dicycloalkylacetylenes: 1,2-Dicyclopropylethyne and (cyclopropylethynyl)cyclobutane (Preprint)
AIR FORCE RESEARCH LAB EDWARDS AFB CA SPACE AND MISSILE PROPULSION DIV
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Lithium acetylides, generated from terminal acetylenes with n-BuLi in THF at -70 degrees C, react chemoselectively with omega-haloalkyl tosylate in the presence of 10 mole of Bu4I at 70 degrees C to furnish omega-haloalkyl acetylenes in very good yields. The omega-haloalkyl acetylenes were subject to intra-molecular alkylation with LDA to provide dicycloalkylethyne.
- Organic Chemistry
- Physical Chemistry