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Radical cyclizations of cyclic ene sulfonamides occur with β-elimination of sulfonyl radicals to form polycyclic imines

Zhang, H and Hay, EB and Geib, SJ and Curran, DP (2013) Radical cyclizations of cyclic ene sulfonamides occur with β-elimination of sulfonyl radicals to form polycyclic imines. Journal of the American Chemical Society, 135 (44). 16610 - 16617. ISSN 0002-7863

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Abstract

Radical cyclizations of cyclic ene sulfonamides provide stable bicyclic and tricyclic aldimines and ketimines in good yields. Depending on the structure of the precursor, the cyclizations occur to provide fused and spirocyclic imines with five-, six-, and seven-membered rings. The initial radical cyclization produces an α-sulfonamidoyl radical that undergoes elimination to form the imine and a phenylsulfonyl radical. In a related method, 3,4-dihydroquinolines can also be produced by radical translocation reactions of N-(2- iodophenylsulfonyl)tetrahydroiso-quinolines. In either case, very stable sulfonamides are cleaved to form imines (rather than amines) under mild reductive conditions. © 2013 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Zhang, H
Hay, EB
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Curran, DPcurran@pitt.eduCURRAN
Date: 6 November 2013
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 135
Number: 44
Page Range: 16610 - 16617
DOI or Unique Handle: 10.1021/ja408387d
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Crystallography, X-Ray; Cyclization; Free Radicals--chemistry; Imines--chemical synthesis; Imines--chemistry; Models, Molecular; Molecular Structure; Polycyclic Compounds--chemical synthesis; Polycyclic Compounds--chemistry; Sulfonamides--chemical synthesis; Sulfonamides--chemistry; Sulfones--chemistry
Other ID: NLM NIHMS535522, NLM PMC3868638
PubMed Central ID: PMC3868638
PubMed ID: 24111991
Date Deposited: 18 Mar 2016 19:47
Last Modified: 19 Jan 2019 14:55
URI: http://d-scholarship.pitt.edu/id/eprint/27267

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