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Phosphorus NMR characterisation of P-N bond rotamers of a α-P4S3 amide with a conformationally constrained chiral substituent

Lookup NU author(s): Dr Bruce Tattershall, Dr Julian Knight

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Abstract

Reactions of bicyclic α-P4S3I2 with Hpthiq gave solutions containing α-P4S3(pthiq)I and α-P4S3(pthiq)2, where Hpthiq is the conformationally constrained chiral secondary amine 1-phenyl-1,2,3,4- tetrahydroisoquinoline. The expected diastereomers have been characterised by complete analysis of their 31P{1H} NMR spectra. Hindered P-N bond rotation in the amide iodide α-P4S3(pthiq)I caused greater broadening of peaks in the room-temperature spectrum of one diastereomer than in that of the other. At 183 K, spectra of two P-N bond rotamers for each diastereomer were observed and analysed. The minor rotamers showed strong evidence for steric crowding, having large diastereomeric differences in 1J(P-P) and 2J(P-S-P) couplings (49 Hz, 16% of value, and 4.4 Hz, 19 % of value, respectively). © 2006 WILEY-VCH Verlag GmbH & Co. KGaA.


Publication metadata

Author(s): Tattershall BW, Knight JG, Andrews MJ, Booth CL

Publication type: Article

Publication status: Published

Journal: Zeitschrift fur Anorganische und Allgemeine Chemie

Year: 2006

Volume: 632

Issue: 3

Pages: 425-432

ISSN (print): 0044-2313

ISSN (electronic): 1521-3749

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA

URL: http://dx.doi.org/10.1002/zaac.200500434

DOI: 10.1002/zaac.200500434


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