Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831, Lough, Alan J. and Stephan, Douglas W. 2013. Boron azides in Staudinger oxidations and cycloadditions. Dalton Transactions 42 (24) , pp. 8674-8683. 10.1039/c3dt50791b |
Abstract
Staudinger reactions of Cy2BN3 with tri-substituted phosphines (R3P) yielded the boron–nitrogen–phosphorus linked systems Cy2BNPR3 (R = Et, tBu, Cy, Ph) (1a–1d respectively). Similarly, reaction of (C6F5)2BN3 with the phosphines PtBu3, PPh3, Ph2PCCPh and Ph2PCCPPh2 yielded (C6F5)2BNPR3 (2a–d respectively). In contrast, the reaction of (C6F5)2BN3 with Ph2P–CCp-tol in the presence of excess Me3SiN3 afforded the bicyclic product 3 [1-(C6F5)2B-4-(p-tol)-1H-1,2,3-triazole-5-P(NH)Ph2] in which both a Staudinger and a cycloaddition reaction has taken place. However, if the Staudinger reaction is prohibited via phosphine oxidation as in the case of (EtO)2P(O)CCP(O)(OEt)2 then the unusual dimeric product 4 [2-(C6F5)2B-4-(P(O)OEt2)-2H-1,2,3-triazole-5-P(O)(OEt)(OB(C6F5)2)] is generated. The structures of 1b–d, 2b–d, 3 and 4 have been determined by X-ray diffraction.
Item Type: | Article |
---|---|
Date Type: | Publication |
Status: | Published |
Schools: | Chemistry |
Subjects: | Q Science > QD Chemistry |
Publisher: | Royal Society of Chemistry |
ISSN: | 1477-9226 |
Date of Acceptance: | 23 April 2013 |
Last Modified: | 27 Oct 2022 09:16 |
URI: | https://orca.cardiff.ac.uk/id/eprint/65042 |
Citation Data
Cited 16 times in Scopus. View in Scopus. Powered By Scopus® Data
Actions (repository staff only)
Edit Item |