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Rotational features of carbon-nitrogen bonds in N-aryl maleimides. Atroposelective reactions of o-tert-butylphenylmaleimides

Curran, DP and Geib, S and DeMello, N (1999) Rotational features of carbon-nitrogen bonds in N-aryl maleimides. Atroposelective reactions of o-tert-butylphenylmaleimides. Tetrahedron, 55 (18). 5681 - 5704. ISSN 0040-4020

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Abstract

Atroposelective addition and cycloaddition reactions of N-2- (tertbutylphenyl)- and N-2,5 (di-tert-butylphenyl)maleimide and a substituted derivative have been studied. Good to excellent stereoselectivities are generally observed, and high rotation barriers (about 29 kcal/mol) prevent the products from inter, converting. Crystal structures of the precursors and products support a straightforward model where reactants attack trans to the o-tert butyl group.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Curran, DPcurran@pitt.eduCURRAN
Geib, S
DeMello, N
Date: 30 April 1999
Date Type: Publication
Journal or Publication Title: Tetrahedron
Volume: 55
Number: 18
Page Range: 5681 - 5704
DOI or Unique Handle: 10.1016/s0040-4020(99)00237-9
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4020
Date Deposited: 29 Jul 2014 21:35
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship-dev.library.pitt.edu/id/eprint/22448

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