relation: http://d-scholarship-dev.library.pitt.edu/19980/
title: A new class of chiral organogermanes derived from C<inf>2</inf>-symmetric dithiols: Synthesis, characterization and stereoselective free radical reactions
creator: Gualtieri, G
creator: Geib, SJ
creator: Curran, DP
description: 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.
date: 2003-06-27
type: Article
type: PeerReviewed
format: text/plain
language: en
rights: attached
identifier: http://d-scholarship-dev.library.pitt.edu/19980/1/licence.txt
identifier:   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     
relation: 10.1021/jo026625s