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Hydroxide displacement of the sulfone linkage in thioxanthen-9-one 10,10-dioxides to benzophenone-2'-hydroxy-2-sulfinic acids. Intramolecular cyclization to xanthones

Bennett, O. Francis and Bouchard, M. J. and Malloy, Richard and Dervin, Peter and Saluti, Gerald (1972) Hydroxide displacement of the sulfone linkage in thioxanthen-9-one 10,10-dioxides to benzophenone-2'-hydroxy-2-sulfinic acids. Intramolecular cyclization to xanthones. Journal of Organic Chemistry, 37 (9). pp. 1356-1359. ISSN 0022-3263. http://resolver.caltech.edu/CaltechAUTHORS:20160516-101234181

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Abstract

2-H, 2,6-diCOOH, 2-CH_3, 2-CH_3O, and 2-NO_2 thioxanthen-9-one 10,10-dioxides were synthesized and treated, at reflux, with 2% NaOH-65% dioxane-H_2O. For these systems, facile hydroxide displacement of the sulfone linkage was found to occur exclusively on the more electrophilic ring to give the novel benzophenone-2’-hydroxy-2-sulfinic acids. Further, in alkaline media, these sulfinic acids generally undergo unique intramolecular cyclization to xanthones. The structures of the sulfinic acids were established by replacement of the sulfinic acid group with a chloromercury group followed by replacement of the latter with hydrogen to afford 2-hydroxybenzophenones.


Item Type:Article
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URLURL TypeDescription
http://dx.doi.org/10.1021/jo00974a015DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo00974a015PublisherArticle
Additional Information:© 1972 American Chemical Society. Received July 22, 1971. This investigation was supported in part by a National Science Foundation Undergraduate Research Grant No. GE 8888.
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Funding AgencyGrant Number
NSFGE 8888
Record Number:CaltechAUTHORS:20160516-101234181
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20160516-101234181
Official Citation:Hydroxide displacement of the sulfone linkage in thioxanthen-9-one 10,10-dioxides to benzophenone-2'-hydroxy-2-sulfinic acids. Intramolecular cyclization to xanthones O. Francis Bennett, M. J. Bouchard, Richard Malloy, Peter Dervin, and Gerald Saluti The Journal of Organic Chemistry 1972 37 (9), 1356-1359 DOI: 10.1021/jo00974a015
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:67125
Collection:CaltechAUTHORS
Deposited By: Victoria Brennan
Deposited On:16 May 2016 20:04
Last Modified:16 May 2016 20:04

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