Issue 4, 2007

The reactions of dialkylgallium hydrides with tert-butylethynylbenzenes—a systematic investigation into the course of hydrogallation reactions

Abstract

The reactions of bis- and tris(tert-butylethynyl)benzenes with dialkylgallium hydrides afforded two different types of products. 1,4-Di(tert-butylethynyl)benzene and dialkylgallium hydrides R2GaH bearing relatively small substituents (R = Et, nPr) gave the expected addition products with each C[triple bond, length as m-dash]C triple bond inserted into a Ga–H bond. The intact GaR2 groups are attached to those carbon atoms which are in α-position to the benzene rings, and intermolecular Ga–C interactions led to the formation of one-dimensional coordination polymers. In contrast secondary reactions with the release of the corresponding trialkylgallium derivatives GaR3 (R = Et, nPr, iPr, CH2tBu, tBu) were observed for all hydrogallation reactions involving the trisalkyne 1,3,5-tris(tert-butylethynyl)benzene. A similar reaction was observed upon treatment of the 1,4-bisalkyne with a dialkylgallium hydride bearing a relatively bulky substituent (R = neopentyl). Cyclophane type molecules are formed in all these cases with two or three gallium atoms in the bridging positions between both benzene rings.

Graphical abstract: The reactions of dialkylgallium hydrides with tert-butylethynylbenzenes—a systematic investigation into the course of hydrogallation reactions

Supplementary files

Article information

Article type
Paper
Submitted
26 Sep 2006
Accepted
13 Nov 2006
First published
23 Nov 2006

Dalton Trans., 2007, 417-423

The reactions of dialkylgallium hydrides with tert-butylethynylbenzenes—a systematic investigation into the course of hydrogallation reactions

W. Uhl, M. Claesener, S. Haddadpour, B. Jasper and A. Hepp, Dalton Trans., 2007, 417 DOI: 10.1039/B614003C

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