Journal of Organic Chemistry p. 3308 - 3314 (1983)
Update date:2022-08-05
Topics:
Hoffman, Robert V.
Buntain, Gregory A.
The addition of p-nitrobenzenesulfonyl peroxide to 3,4-dihydro-2H-pyran (DHP) in alcohols gives high yields of 3-<<(p-nitrophenyl)sulfonyl>oxy>-2-alkoxytetrahydropyrans.The stereochemistry of the addition process is dependent on the steric bulk of the attacking alcohol.For small alcohols, trans addition predominates, while bulky alcohols give mostly cis product.The results are compared with analogous haloalkoxylations of DHP.
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(1983)
