Hydroboration. 70. The polycyclic hydroboration of acyclic and cyclic trienes with borane in tetrahydrofuran and triethylamine-borane. Reexamination of the …

HC Brown, E Negishi, WC Dickason

Index: Brown, Herbert C.; Negishi, Ei-ichi; Dickason, William C. Journal of Organic Chemistry, 1985 , vol. 50, # 4 p. 520 - 527

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Citation Number: 11

Abstract

The hydroboration of 1, 4, 8-nonatriene (l), 5-methyl-1, 4, 8-nonatriene (2), 1, 3, 7-octatriene (3), and trans,-trans, truns-1, 5, 9-cyclododecatriene (4) with borane in tetrahydrofuran (THF) and triethylamine-borane was studied. The hydroboration of the acyclic trienes with borane in THF at 0" C produced monomeric bicyclic boranes in low yields. Moreover, thermodynamically stable organoboranes with fused six-membered rings, such as 9- ...