Hydroboration. 86. Convenient conversion of aldehydes and ketones into the corresponding alkenes via hydroboration of their enamines. A remarkably simple …
B Singaram, MV Rangaishenvi, HC Brown…
Index: Singaram, Bakthan; Rangaishenvi, Milind V.; Brown, Herbert C.; Goralski, Christian G.; Hasha, Dennis L. Journal of Organic Chemistry, 1991 , vol. 56, # 4 p. 1543 - 1549
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Citation Number: 31
Abstract
Aldehydes and ketones are converted into the corresponding alkenes via hydroboration of their enamines. Hydroboration of aldehyde enamines by 9-borabicyclo [3.3. llnonane (g- BBN), followed by methanolysis, affords the corresponding terminal alkenes in 7590% yields. Unsaturated aldehyde enamines produce the corresponding dienes under these conditions. Enamines derived. from substituted cyclic ketones and heterocyclic ketones ...
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