Hydroboration. XXXIII. Cyclic hydroboration of 1, 4-pentadiene with borane in tetrahydrofuran. Thermal behavior of the organoborane derivatives and a simple …

E Negishi, PL Burke, HC Brown

Index: Negishi,E. et al. Journal of the American Chemical Society, 1972 , vol. 94, p. 7431 - 7437

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Citation Number: 21

Abstract

Abstract: The hydroboration of 1, Cpentadiene with borane in tetrahydrofuran in the 3: 2 molar ratio produces in 72% yield a mixture of at least six 3: 2 compounds. Oxidation of the product provides 1, 5-and 1, 4-pentanediols in a ratio of 42: 58. Thermal treatment of the 3: 2 product at 170", followed by oxidation, yields 1, 5-and 1, 4-pentanediols and 1-pentanol in a ratio of approximately 80: lO: lO. The reaction of the thermally treated 3: 2 product with an ...