Reaction of 3-alkenols with thallium trinitrate: An unexpected and useful ring contraction

Article abstract of DOI:10.1080/00397910008087377

The first thallium trinitrate (TTN) mediated ring contraction of cyclic homoallylic alcohols, using a 1:1 mixture of AcOH and H₂O as solvent, is described. The reaction of two of these alcohols with excess of TTN in pentane gave α-spirocyclopentyl-γ-butirolactones in reasonable yields.

Full text of DOI:10.1080/00397910008087377

This article was downloaded by: [Northeastern University]
On: 09 October 2014, At: 16:52
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
Reaction of 3-Alkenols with
Thallium Trinitrate: An
Unexpected and Useful Ring
Contraction
Helena M. C. Ferraz a , Andréa P. Santos a , Luiz F.
Silva Jr. a & Tiago de O. Vieira a
a Instituto de Química, Universidade de São Paulo ,
C.P. 26077 05599--970, São Paulo, SP, Brasil E-mail:
Published online: 04 Dec 2007.
To cite this article: Helena M. C. Ferraz , Andréa P. Santos , Luiz F. Silva Jr. & Tiago
de O. Vieira (2000) Reaction of 3-Alkenols with Thallium Trinitrate: An Unexpected
and Useful Ring Contraction, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 30:4, 751-762, DOI:
10.1080/00397910008087377
To link to this article: http://dx.doi.org/10.1080/00397910008087377
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