eprintid: 20505
rev_number: 16
userid: 1418
dir: disk0/00/02/05/05
datestamp: 2014-02-13 18:56:27
lastmod: 2019-02-02 15:58:23
status_changed: 2014-02-13 18:56:27
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Stalinski, K
creators_name: Curran, DP
creators_email: 
creators_email: curran@pitt.edu
creators_id: 
creators_id: CURRAN
title: Stereocontrol at the steady state in radical cyclizations of acyclic dihalides
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
abstract: The first examples of manipulating stereocontrol solely by reaction topography in radical cyclizations starting from acyclic precursors are reported. The kinetic model for acyclic compound stereoselection is verified experimentally by conducting a series of radical cyclizations of 1,3-dihalo-2-(1-phenyl-3-butynyl)propanes with triphenyltin hydride and measuring the ratios of the products. Monohalide intermediates are observed for the first time, and evidence that bromide- and iodide-substituted radicals have different cyclization rate constants is provided.
date: 2002-05-03
date_type: published
publication: Journal of Organic Chemistry
volume: 67
number: 9
pagerange: 2982 - 2988
refereed: TRUE
issn: 0022-3263
id_number: 10.1021/jo011056u
pmid: 11975556
citation:   Stalinski, K and Curran, DP  (2002) Stereocontrol at the steady state in radical cyclizations of acyclic dihalides.  Journal of Organic Chemistry, 67 (9).  2982 - 2988.  ISSN 0022-3263     
document_url: http://d-scholarship-dev.library.pitt.edu/20505/1/licence.txt