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Stereocontrol at the steady state in radical cyclizations of acyclic dihalides

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

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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.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Stalinski, K
Curran, DPcurran@pitt.eduCURRAN
Date: 3 May 2002
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 67
Number: 9
Page Range: 2982 - 2988
DOI or Unique Handle: 10.1021/jo011056u
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
PubMed ID: 11975556
Date Deposited: 13 Feb 2014 18:56
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/20505

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