Tetrahedron

Radical reactions of bicyclo [2.2. 1] heptan-3-spiro-2′-oxiranes

WR Bowman, DS Brown, CA Burns, BA Marples…

文献索引：Bowman, W. Russell; Brown, David S.; Burns, Catherine A.; Marples, Brian A.; Zaidi, Naveed A. Tetrahedron, 1992 , vol. 48, # 33 p. 6883 - 6896

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被引用次数: 17

摘要

Tributyltin hydride reduction of 2-bromo-and 2-keto-bicyclo [2.2. 1] heptan-3-spiro-2′- oxiranes gives ring opening of the oxirane-rings 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 ...