Journal of Organic Chemistry p. 3119 - 3123 (1981)
Update date:2022-09-26
Topics:
Meyers, A. I.
Lawson, Jon P.
Carver, David R.
The reaction of vinyltri-n-butylphosphonium salts, aldehydes, and sodiophthalimide in THF gave good yields of the allylic phthalimides with high E stereoselectivity (75-100percent).The use of the vinyltriphenylphosphonium salts (Schweizer reaction) gave the allyl phthalimide with the Z isomer predominating.A study of the phthalimide cation and the effect of added lithium salt showed some reversal in the olefin geometry but in general the selectivity was only 3:1
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