On the reaction of (dibromomethyl) lithium with bicyclic and tricyclic ketones

DS Teager, HD Ward, RK Murray Jr

Index: Teager, David S.; Ward, Harry D.; Murray, Roger K. Journal of Organic Chemistry, 1993 , vol. 58, # 20 p. 5493 - 5499

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Citation Number: 2

Abstract

Many literature examples show that the reaction of a simple cyclic ketone with (dibromomethy1)-lithium at-78 OC, followed by low-temperature hydrolysis of the resulting lithium alkoxide 33, gives the corresponding dibromomethyl alcohol. We have found that the reaction of a bicyclic or tricyclic ketone with (dibromomethy1) lithium under comparable conditions provides a dibromomethyl alcohol and/or an a-bromo aldehyde. The latter ...