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

PDF - Published Version Restricted to SRO admin only until 11 September 2019. Download (821kB)

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
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:	06 Dec 2018 14:23
URI:	http://sro.sussex.ac.uk/id/eprint/78884

View download statistics for this item

📧 Request an update