Synthesis of 2-acetylenic carboxylic acids, 1-sulfinyl and 1-sulfonyl- 2-ketones from 2-acetylenic phenyl sulfides

Article abstract of DOI:10.1080/00397919708005006

Monochlorination at the 1-position with sulfuryl chloride, followed by methanolysis converted 2-acetylenic phenyl sulfides into 1-methoxy-2- acetylenic phenyl sulfides. Oxidation with chromic acid gave 2-acetylenic carboxylic acids. Oxidation of 2-acetylenic phenyl sulfides with Oxone and hydrogen peroxide in acetic acid gave the corresponding sulfoxides and sulfones respectively. Diethylamine addition to the triple bond produced enamines which were hydrolyzed with aqueous hydrochloric acid to the corresponding 1-sulfinyl and 1-sulfonyl-2-ketones.

Full text of DOI:10.1080/00397919708005006

This article was downloaded by: [Stony Brook University]
On: 17 October 2014, At: 07:06
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH,
UK
Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
Synthesis of 2-Acetylenic
Carboxylic Acids, 1-Sulfinyl and
1-Sulfonyl-2-ketones from 2-
Acetylenic Phenyl Sulfides
Carlos C. Fortes a & Clevia F.D. Garrote a
a Departamento de Química , Universidade de
Brasília , 70919.970 - CP 04478, Brasilia, DF, Brazil
Published online: 22 Aug 2006.
To cite this article: Carlos C. Fortes & Clevia F.D. Garrote (1997) Synthesis
of 2-Acetylenic Carboxylic Acids, 1-Sulfinyl and 1-Sulfonyl-2-ketones from 2-
Acetylenic Phenyl Sulfides, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 27:17, 2993-3026, DOI:
10.1080/00397919708005006
To link to this article: http://dx.doi.org/10.1080/00397919708005006
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the
information (the “Content”) contained in the publications on our platform.
However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness,
or suitability for any purpose of the Content. Any opinions and views
expressed in this publication are the opinions and views of the authors, and
are not the views of or endorsed by Taylor & Francis. The accuracy of the
Content should not be relied upon and should be independently verified with

primary sources of information. Taylor and Francis shall not be liable for any
losses, actions, claims, proceedings, demands, costs, expenses, damages,
and other liabilities whatsoever or howsoever caused arising directly or
indirectly in connection with, in relation to or arising out of the use of the
Content.
This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan,
sub-licensing, systematic supply, or distribution in any form to anyone is
expressly forbidden. Terms & Conditions of access and use can be found at
http://www.tandfonline.com/page/terms-and-conditions