Addition of cyclic ethers and acetals to ethyl 3,3-difluoro-2-methylpropenoate

Ethyl 3,3-difluoro-2-methylpropenoate forms 1 : 1 adducts with tetrahydrofuran and 1,3-dioxolanes under free radical conditions. In contrast no 1 : 1 adducts are observed when tetrahydropyran and 1,3-dioxanes are used as sources of α-alkoxy radicals. An explanation is presented based on FMO and radi...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2000-03, Vol.102 (1), p.345-348
Main Authors: Bumgardner, Carl L., Burgess, Jason P.
Format: Article
Language:English
Subjects:
Acetals
Cyclic ethers
Ethyl
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Summary:Ethyl 3,3-difluoro-2-methylpropenoate forms 1 : 1 adducts with tetrahydrofuran and 1,3-dioxolanes under free radical conditions. In contrast no 1 : 1 adducts are observed when tetrahydropyran and 1,3-dioxanes are used as sources of α-alkoxy radicals. An explanation is presented based on FMO and radical stability arguments.
ISSN:0022-1139
1873-3328
DOI:10.1016/S0022-1139(99)00300-0