Journal of Organic Chemistry p. 652 - 657 (1987)
Update date:2022-08-29
Topics:
Shao, Rui-lian
Peters, Dennis G.
In dimethylformamide containing tetramethylammonium perchlorate, cyclic voltammograms for reduction of 1-iodo-5-decyne and 1-bromo-5-decyne at a vitreous carbon electrode each consist of a single irreversible wave due to two-electron scission of the carbon-halogen bond.Preparative-scale electrolyses of 1-iodo-5-decyne yield pentylidenecyclopentane, 5-decyne, 1-decen-5-yne, and a small amount of 5-decyn-1-ol, whereas reduction of 1-bromo-5-decyne affords mainly 5-decyne and 1-decen-5-yne along with a modest quantity of pentylidenecyclopentane.Differences in product distributions correlate with the extent to which the 5-decyn-1-yl radical persists as a transient species.Pentylidenecyclopentane arises via intramolecular cyclization of the 5-decyn-1-yl radical followed by hydrogen atom abstraction, 5-decyne is formed via protonation of the 5-decyn-1-yl carbanion by either water or the tetramethylammonium cation, and 1-decen-5-yne and 5-decyn-1-ol are obtained, respectively, via E2 and SN2 reactions between unreduced starting material and hydroxide ion (generated by deprotonation of water).In the presence of a proton donor (diethyl malonate or hexafluoroisopropyl alcohol), the quantities of pentylidenecyclopentane and 5-decyne rise noticeably and the yield of 1-decen-5-yne falls dramatically.
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