Alcoholysis of Epoxides Catalyzed by Tetracyanoethylene and Dicyanoketene Acetals
- 1 January 1996
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 69 (1) , 195-205
- https://doi.org/10.1246/bcsj.69.195
Abstract
A typical π-acid tetracyanoethylene and capto-dative olefin dicyanoketene acetals were found to catalyze stereospecific alcoholysis of epoxides at the ambient temperature to 50 °C in good yields. Mildness and significant chemoselectivity of the catalysts were demonstrated by intactness of tetrahydropyranyl ether and ethylene acetal groups. A novel regioselectivity associated with anchimeric assistance of the ethereal group on the side chain was observed in the ring opening reaction of the 1,2-disubstituted epoxides.Keywords
This publication has 30 references indexed in Scilit:
- 2,3-Dichloro-5,6-dicyano-p-benzoquinone as a Mild and Efficient Catalyst for the Tetrahydropyranylation of AlcoholsBulletin of the Chemical Society of Japan, 1992
- Ceric ammonium nitrate, an efficient catalyst for mild and selective opening of epoxides in the presence of water thiols and acetic acidTetrahedron, 1991
- Efficient, mild, and regioselective conversion of thiiranes to alkoxy and acetoxy disulphides and dithianes with Ce(IV) based oxidantsTetrahedron, 1991
- Mild, Efficient and Selective Opening of Epoxides with Alcohols Catalyzed by Ceric(IV) Ammonium NitrateSynthetic Communications, 1990
- 2,3-Dichloro-5,6-Dicyano-p-Benzoquinone, an efficient, mild, neutral and highly regioselective catalyst for alcoholysis of epoxidesTetrahedron Letters, 1990
- Organotin phosphate condensates as a catalyst of selective ring-opening of oxiranes by alcoholsThe Journal of Organic Chemistry, 1988
- Titanium isopropoxide-mediated nucleophilic openings of 2,3-epoxy alcohols. A mild procedure for regioselective ring-openingThe Journal of Organic Chemistry, 1985
- Nucleophilic opening of 2,3-epoxy acids and amides mediated by titanium isopropoxide. Highly enhanced C-3 selectivityThe Journal of Organic Chemistry, 1985
- Recent advances in the preparation and synthetic applications of oxiranesTetrahedron, 1983
- Organic reactions at alumina surfaces. Mild and selective opening of arene and related oxides by weak oxygen and nitrogen nucleophilesJournal of the American Chemical Society, 1977