Journal of Organic Chemistry p. 3094 - 3097 (1982)
Update date:2022-08-02
Topics:
Oakes, Fred T.
Yang, Fu-An
Sebastian, John F.
2,3,4,5-Tetrahydrooxepin treated with either n-butyllithium or tert-butyllithium affords 7-lithio-2,3,4,5-tetrahydrooxepin.The question of allylic vs. vinylic deprotonation of cyclic vinyl ethers was examined by varying ring size and degree of unsaturation.Carbon-13 spectral data for the anions obtained from 2,5-dihydrofuran, 2,3-dihydrooxepin, and 2,3,4,5-tetrahydrooxepin are reported.In contrast to 2,3,4,5-tetrahydrooxepin, 2,3-dihydrooxepin undergoes allylic deprotonation, possibly as a result of a slightly larger C-C=C bond angle in the dihydrooxepin as compared to that of the tetrahydrooxepin.
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Doi:10.1016/S0022-328X(00)86780-7
(1982)Doi:10.1016/S0040-4039(00)88391-4
(1983)Doi:10.1246/bcsj.55.1121
(1982)Doi:10.1039/c1cc10411j
(2011)Doi:10.1016/j.bmcl.2004.09.079
(2004)Doi:10.1021/jo00139a010
(1982)