Tetrahedron

Base-induced cyclizations. Reactions of the 1-halo-6-(2-hydroxyethoxy)-cyclohexenes with potassium t-butoxide

AT Bottini, FP Corson, KA Frost, W Schear

文献索引：Bottini,A.T. et al. Tetrahedron, 1972 , vol. 28, p. 4701 - 4710

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被引用次数: 3

摘要

Reactions of 1-bromo-6-(2-hydroxyethoxy) cyclohexene (2) and its chloro analog 3 with potassium t-butoxide in dimethyl sulfoxide at 60–70° gave cyclohex-2-enone ethylene ketal (7) and cis-2, 5-dioxabicyclo [4.4. 0] dec-7-ene (8) as the major products. Under these conditions, 1-(2-hydroxyethoxy)-1, 4-cyclohexadiene (13) is also converted to 7 and elimination products, benzene and ethylene glycol. Conversion of 13 to 7 was shown to ...