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Boron azides in Staudinger oxidations and cycloadditions

Melen, Rebecca L., 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

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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: 04 Jun 2017 06:49
URI: http://orca.cf.ac.uk/id/eprint/65042

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