1,4-Pentadienyl-3-sulfonamides: Frameworks for “Disfavored” Radical Cascade Cyclizations
- 12 September 2001
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (21) , 3405-3407
- https://doi.org/10.1021/ol0166449
Abstract
[reaction: see text]. 1,4-pentadienyl-3-sulfonamides afford products including those resulting from disfavored 5-endo-trig reactions when subjected to radical cyclization conditions. Products resulting from pathways featuring 4-exo-trig cyclizations are also detected, even when the 4-exo-trig reaction leads to a highly strained bicyclo[3.2.0] ring system.Keywords
This publication has 10 references indexed in Scilit:
- Reaction of Highly Methylated 2-Methylenecycloalkyl Hydroperoxides with FeSO4/CuCl2. Remarkably Efficient 5-endo-trigor 6-endo-trigCyclization of the Intermediate Carbon RadicalsThe Journal of Organic Chemistry, 1999
- Electrochemical Catalysis of a 5-Endo-Trig Cyclization in Bicontinuous MicroemulsionsThe Journal of Organic Chemistry, 1998
- Atom transfer cyclization reactions of .alpha.-iodo esters, ketones, and malonates: examples of selective 5-exo, 6-endo, 6-exo, and 7-endo ring closuresThe Journal of Organic Chemistry, 1989
- Regio-selectivity and stereo-selectivity in radical reactionsTetrahedron, 1981
- 5-Endo-trigonal reactions: a disfavoured ring closureJournal of the Chemical Society, Chemical Communications, 1976
- Free radical addition of isobutyric acid to α,ω-diolefins. A new route to α,α,α′,α′-tetramethylalkanedioic acidsJournal of the Chemical Society, Perkin Transactions 2, 1973
- Radikalische Umlagerungen in einigen bicyclischen SystemenEuropean Journal of Inorganic Chemistry, 1971
- Photochemistry of Steroid 4-en-3-one 11α-Nitrites. A Novel Synthesis of A-Nor-B-homo SteroidsCanadian Journal of Chemistry, 1971
- Methoxymercurierung von bullvalen und bicyclo[4.2.2]deca-2,4,7,9-tetraenTetrahedron Letters, 1970
- Free-Radical-Induced Cyclization of ι-Phenyl-1-alkenes1The Journal of Organic Chemistry, 1966