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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 5
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Original Articles

Regiospecific Functionalization of Cyclic Allenes with Catecholeorane

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Pages 437-442 | Received 15 Dec 1978, Published online: 06 Dec 2006
 

Abstract

Reaction of diborane1 and disiamylborane2 with cyclic allenes, resulted in the formation of a mixture of products resulting from the addition of boron at the central carbon as well as terminal carbon. Fish has reported that addition of 4, 4, 6-trimethyl-1, 3, 2-dioxaborinane to 1, 3-disubstituted allenes takes place at the central carbon atom preferentially when the hydroboration was done at 130° for 35–50 h in a sealed tube.3 The reactivity and stability of catecholborane at high temperatures which is known to provide greater stearic

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