Stennett, Tom, Mattock, James D, Pentecost, Leanne, Vargas, Alfredo and Braunschweig, Holger (2018) Chelated diborenes and their inverse-electron-demand Diels-Alder reactions with dienes. Angewandte Chemie International Edition, 57 (46). pp. 15276-15281. ISSN 1521-3773
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Abstract
A doubly base-stabilized diborane based on a benzylphosphine linker was prepared by a salt elimination reaction between 2-LiC6H4CH2PCy2.Et2O and B2Br4. This compound was reduced with KC8 to its corresponding diborene, with the benzylphosphine forming a five-membered chelate. The diborene reacts with butadiene, 2-trimethylsiloxy-1,3-butadiene and isoprene to form 4,5-diboracyclohexenes, which interconvert between their 1,1- (geminal) and 1,2- (vicinal) chelated isomers. The 1,1-chelated diborene undergoes a halide-catalysed isomerisation into its thermodynamically favoured 1,2-isomer, which undergoes Diels-Alder reactions more slowly than the kinetic product.
Item Type: | Article |
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Schools and Departments: | School of Life Sciences > Chemistry |
Subjects: | Q Science > QD Chemistry |
Depositing User: | Alfredo Vargas |
Date Deposited: | 20 Sep 2018 13:53 |
Last Modified: | 11 Sep 2019 01:00 |
URI: | http://sro.sussex.ac.uk/id/eprint/78884 |
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