eprintid: 20619
rev_number: 16
userid: 1418
dir: disk0/00/02/06/19
datestamp: 2014-02-21 21:03:22
lastmod: 2019-02-02 15:58:54
status_changed: 2014-02-21 21:03:22
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Haney, BP
creators_name: Curran, DP
creators_email:
creators_email: curran@pitt.edu
creators_id:
creators_id: CURRAN
title: Round trip radical reactions from acyclic precursors to tricyclo[5.3.1.02,6]undecanes. A new cascade radical cyclization approach to (±)-isogymnomitrene and (±)-gymnomitrene
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
abstract: The synthesis and 'round trip radical cyclization' of 11-iodo-2,7,11- trimethyldodec-6-en-5-one are described. The round trip cyclization is a sequence of 5-exo, 6-endo, and 5-exo cyclizations in which the last radical cyclization occurs at the same carbon atom as the initial radical generation. The key second (6-endo) cyclization produces two stereoisomers, one of which cyclizes efficiently to isogymnomitrene ketone, while the other cyclizes inefficiently to gymnomitrene ketone. Efforts to influence the kinetic or thermodynamic outcome of the second cyclization were not successful, and the results are contrasted with a related cyclization of Jung and Rayle where thermodynamic control was readily established.
date: 2000-04-07
date_type: published
publication: Journal of Organic Chemistry
volume: 65
number: 7
pagerange: 2007 - 2013
refereed: TRUE
issn: 0022-3263
id_number: 10.1021/jo9914871
pmid: 10841670
mesh_headings: Bridged Compounds--chemical synthesis
mesh_headings: Cyclization
mesh_headings: Free Radicals--chemistry
mesh_headings: Stereoisomerism
chemical_names: Bridged Compounds
chemical_names: Free Radicals
citation: Haney, BP and Curran, DP (2000) Round trip radical reactions from acyclic precursors to tricyclo[5.3.1.02,6]undecanes. A new cascade radical cyclization approach to (±)-isogymnomitrene and (±)-gymnomitrene. Journal of Organic Chemistry, 65 (7). 2007 - 2013. ISSN 0022-3263
document_url: http://d-scholarship-dev.library.pitt.edu/20619/1/licence.txt