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Comparison of the conformation in the crystal and in solution of 1-(nitromethyl)-3-phenylphthalan

Smith, Robert A. and Parker, Richard G. and Roberts, John D. (1970) Comparison of the conformation in the crystal and in solution of 1-(nitromethyl)-3-phenylphthalan. Tetrahedron Letters, 11 (21). pp. 1763-1766. ISSN 0040-4039. https://resolver.caltech.edu/CaltechAUTHORS:20151026-093704589

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Abstract

In connection with the stereochemical problem posed by 1, 3-disubstituted phthalans, we have determined the crystal structure of trans-1-(nitromethyl)-3_phenylphthalan, I (2). In the crystal, the dihedral angle between the C-H_X and the C-NO_2 bonds is found to be 90” with the nitro group oriented away from the phthalan part of the molecule. It is of special interest to determine whether the same conformation is also favored in solution and to this end we have analyzed the proton magnetic resonance spectra of I in CDCl_3.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/S0040-4039(01)98077-3DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040403901980773PublisherArticle
Additional Information:© 1970 Pergamon Press. Received in USA 12 March 1970; received in UK for publication 6 April 1970. The work carried on at the California Institute of Technology was supported by the National Science Foundation.
Issue or Number:21
Record Number:CaltechAUTHORS:20151026-093704589
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151026-093704589
Official Citation:Robert A. Smith, Richard G. Parker, John D. Roberts, Comparison of the conformation in the crystal and in solution of 1-(nitromethyl)-3-phenylphthalan, Tetrahedron Letters, Volume 11, Issue 21, 1970, Pages 1763-1766, ISSN 0040-4039, http://dx.doi.org/10.1016/S0040-4039(01)98077-3. (http://www.sciencedirect.com/science/article/pii/S0040403901980773)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61516
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 22:07
Last Modified:03 Oct 2019 09:08

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