Journal of Organic Chemistry p. 1258 - 1267 (1982)
Update date:2022-08-02
Topics:
Liotta, Dennis
Zima, George
Saindane, Manohar
The regio- and stereoselectivity of phenylselenenyl chloride additions to allylic alcohols and their derivatives have been systematically studied.On the basis of the results, a mechanism involving two basic premises is proposed.These are as follows: (a) allylic oxygen's direct selenonium ion formation to the syn face of the double bond; (b) axial attack of the chloride ion is kinetically favored over equatorial attack.A series of rules which are useful for predicting the regio- and stereoselectivity of phenylselenenyl chloride additions to allylic systems are discussed.In addition, these reactions can be used as the key step in a general 1,3-enone transposition sequence.Several examples of this transposition sequence are illustrated.
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(1989)Doi:10.1021/ja01252a039
(1943)Doi:10.1248/cpb.42.1157
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(2000)Doi:10.1007/BF00958404
(1982)Doi:10.1016/S0022-328X(00)85843-X
(1982)