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A new class of chiral organogermanes derived from C<inf>2</inf>-symmetric dithiols: Synthesis, characterization and stereoselective free radical reactions

Gualtieri, G and Geib, SJ and Curran, DP (2003) A new class of chiral organogermanes derived from C<inf>2</inf>-symmetric dithiols: Synthesis, characterization and stereoselective free radical reactions. Journal of Organic Chemistry, 68 (13). 5013 - 5019. ISSN 0022-3263

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Abstract

A new class of dithiostannanes and dithiogermanes have been prepared from 1,1′-binaphthyl-2,2′-dithiol and 3,3′-bis(trimethylsilyl)-1,1′ -binaphtho-2,2′-dithiol. While reduction of 4-butyl-4-chloro-3,5-dithia-4-stanna-cyclohepta[2,1-a;3,4- a′]dinaphthalene to the corresponding tin hydride was unsuccessful, 4-tert-butyl-3,5-dithia-4-germa-cyclohepta [2,1-a;3,4-a′]dinaphthalene and 4-tert-butyl- 2,6-bis(trimethylsilyl) -3,5-dithia-4-germa-cyclohepta[2,1-a;3,4-a′]dinaphthalene were obtained by reduction of the parent germanium chlorides with NaBH4 and LiBH4, respectively. Kinetic constants for hydrogen transfer to a primary alkyl radical were measured for both germanium hydrides. Reduction of α-halo carbonyl compounds by these germanium hydrides occurs with moderate ee values (up to 42%), while hydrogermylation of methyl methacrylate occurs with low selectivity (<3/1) for the former hydride but high selectivity (> 10/1) for the latter.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Gualtieri, G
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Curran, DPcurran@pitt.eduCURRAN
Date: 27 June 2003
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 68
Number: 13
Page Range: 5013 - 5019
DOI or Unique Handle: 10.1021/jo026625s
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
PubMed ID: 12816453
Date Deposited: 07 Nov 2013 20:55
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/19980

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