Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5231174 | Tetrahedron | 2007 | 14 Pages |
Abstract
Vinylic halides having alcohol, sulfonamide, active methine, and thiol moieties as nucleophiles cyclize to hetero- and carbocycles by intramolecular nucleophilic substitution at the sp2 carbon centers. The density functional theory calculations suggest that the cyclization proceeds through SN2-type substitution (the in-plane vinylic nucleophilic substitution, SNVÏ), when vinyl halides are substituted with oxygen, nitrogen, and carbon nucleophiles. The substitution with sulfur nucleophiles, in contrast, proceeds through both routes of SNVÏ and out-of-plane vinylic nucleophilic substitution (SNVÏ).
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Hironori Miyauchi, Shunsuke Chiba, Koji Fukamizu, Kaori Ando, Koichi Narasaka,