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- W2952647767 abstract "The reaction of trialkylboranes with ω-tosyloxy-1-lithio-1-alkynes can induce transfer of an alkyl group from the boron atom to the alkynyl carbon atom with concomitant formation of four- through six-membered carbocycles via intramolecular displacement of the ω-tosyloxy group. The stereoselectivity of the reaction, however, is low (anti/syn≃1.6–1.7). The corresponding reaction of ω-halo- or ω-tosyloxy-1-alkenylborates also gives exocyclic alkenes via 1,2-migration-cyclization followed by dehydroboration. In the cases of cyclopropanation, cyclopropylcarbinyl-to-homopropargyl rearrangement rather than dehydroboration takes place. Diphenylzirconocene reacts similarly with 6-lithio-5-hexynyl tosylate to give phenylmethylenecyclopentane in 45% yield. On the other hand, attempts to induce a similar migration with phenyl derivatives of Y, V, Cr, and Mn have led to < 5–10% yields of the same cyclization product." @default.
- W2952647767 created "2019-06-27" @default.
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- W2952647767 date "2010-08-20" @default.
- W2952647767 modified "2023-09-26" @default.
- W2952647767 title "ChemInform Abstract: Cyclization Reactions of ω-Tosyloxy-1-alkynyl- and ω- Tosyloxy-1-alkenylborates and Their ω-Halo Analogues." @default.
- W2952647767 cites W2166591076 @default.
- W2952647767 doi "https://doi.org/10.1002/chin.199343100" @default.
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