Tetrahedron p. 6883 - 6896 (1992)
Update date:2022-07-30
Topics:
Bowman, W. Russell
Brown, David S.
Burns, Catherine A.
Marples, Brian A.
Zaidi, Naveed A.
Tributyltin hydride reduction of 2-bromo- and 2-keto-bicyclo<2.2.1>heptan-3-spiro-2'-oxiranes gives ring opening of the oxirane-ringes via intermediate 3-(spiro-2'-oxiranyl)bicyclo<2.2.1>heptan-2-yl radicals, whereas reduction of the analogous 2-(thiocarbonyl)imidazolides)<2(O-CS-Im)> unusually yields the 2-methoxy derivatives and does not proceed by the expected normal fragmentation to yield 3-(spiro-2'-oxiranyl)bicyclo<2.2.1>heptan-2-yl radicals and subsequent ring-opening of the oxirane rings.
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Doi:10.1016/j.ejmech.2013.03.008
(2013)Doi:10.1016/j.ejmech.2013.03.001
(2013)Doi:10.1016/0223-5234(92)90151-P
(1992)Doi:10.1039/c39920001128
(1992)Doi:10.1016/j.saa.2013.04.016
(2013)Doi:10.1016/S0040-4020(01)89441-2
(1992)
