Reaction of organoboranes with 2-bromoacrolein. A facile one-stage synthesis of. alpha.-bromo aldehydes

HC Brown, GW Kabalka, MW Rathke…

Index: Brown,H.C. et al. Journal of the American Chemical Society, 1968 , vol. 90, p. 4165 - 4166

Full Text: HTML

Citation Number: 29

Abstract

Although the major product from solvolysis of either 3-nortricyclyl tosylate (IX) or 5-norborn-2- enyl tosylate is 3-nortricyclyl acetate, some 5-norborn-2-enyl acetate also is formed. 7a,* By analogy, it might have been expected that some conversion of I to I1 and eventually to I11 might have occurred, with attendant deuterium scrambling. The nonobservance of such scrambling, at least under the conditions employed, shows that" leakage" to I1 (and to 111 ...