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Investigation of the reductive cleavage of BINAP and application to the rapid synthesis of phospholes

journal contribution
posted on 2023-06-08, 15:49 authored by Chris W D Gallop, Mariusz Bobin, Petra Hourani, Jessica Dwyer, S Mark Roe, Eddy Viseux
A rapid and easy entry into ?3-phospholes and ?4- phosphole oxides derived from BINAP is reported herein featuring a variety of C and Si substituents and functional groups, as well the investigative work on the mechanistic pathway. DFT calculations using B3LYP functionals have been carried out to rationalize the mechanism. The observed experimental 31P resonance shifts were compared with the calculated shifts of the proposed intermediates after calibration of the shielding tensors. The calculations included the use of polarizable continuum models to take into account solvent effects and were found to be in excellent agreement, providing further evidence for the proposed mechanism.

History

Publication status

  • Published

Journal

Journal of Organic Chemistry

ISSN

0022-3263

Publisher

American Chemical Society

Issue

13

Volume

78

Page range

6522-6528

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2013-09-18

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