1,4-pentadienyl-3-sulfonamides: frameworks for "disfavored" radical cascade cyclizations

S Bommezijn; C G Martin; A R Kennedy; D Lizos; J A Murphy

doi:10.1021/ol0166449

1,4-pentadienyl-3-sulfonamides: frameworks for "disfavored" radical cascade cyclizations

Org Lett. 2001 Oct 18;3(21):3405-7. doi: 10.1021/ol0166449.

Authors

S Bommezijn¹, C G Martin, A R Kennedy, D Lizos, J A Murphy

Affiliation

¹ Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, UK.

PMID: 11594845
DOI: 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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkadienes / chemistry
Cyclization
Free Radicals
Sulfonamides / chemical synthesis*

Substances

Alkadienes
Free Radicals
Sulfonamides