Studies on chiral thiophosphoric acids and their derivatives 14. The asymmetric cyclization of (+)-cis-1,2,2-trimethyl-1,3-diaminocyclopentane with thiophosphorodichloridates and o-(4-nitrophenyl)thiophosphorochloridates

Article abstract of DOI:10.1080/10426509608046418

The cyclization of (+)-cis-1,2,2-trimethyl-1,3-diaminocyclopentane 1 with thiophosphorodichloridates 2 or O-(4-nitrophenyl)thiophosphorochloridates 4 forms (+)-2,4,5-diazaphosphabicyclo[3.2.1]octane 3 and 3′, respectively, but the stereoselectivity arising from the condensation of (+)-1 with 4 is less than that of (+)-1 with 2. The distinction between the two product distributions might be due to the significance of different mechanistic routes. In the light of a trigonal bipyramid (TBP) intermediate and Berry pseudorotation (BPR) concept their mechanism are discussed.

Full text of DOI:10.1080/10426509608046418

This article was downloaded by: [Michigan State University]
On: 30 December 2014, At: 17:56
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
Phosphorus, Sulfur, and Silicon and the
Related Elements
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/gpss20
STUDIES ON CHIRAL THIOPHOSPHORIC
ACIDS AND THEIR DERIVATIVES 14.
THE ASYMMETRIC CYCLIZATION
OF (+)-CIS-1,2,2-TRIMETHYL-1,3-
DIAMINOCYCLOPENTANE WITH
THIOPHOSPHORODICHLORIDATES AND O-
(4-
NITROPHENYL)THIOPHOSPHOROCHLORIDATE
Chu-Chi Tang a , Hui-Fang Lang a , Zheng-Jie He a & Ru-Yu Chen a
a Institute of Elemento-Organic Chemistry, Nankai University ,
Tianjin, 300071, P.R. China
Published online: 04 Oct 2006.
To cite this article: Chu-Chi Tang , Hui-Fang Lang , Zheng-Jie He & Ru-Yu Chen (1996) STUDIES ON
CHIRAL THIOPHOSPHORIC ACIDS AND THEIR DERIVATIVES 14. THE ASYMMETRIC CYCLIZATION OF (+)-
CIS-1,2,2-TRIMETHYL-1,3- DIAMINOCYCLOPENTANE WITH THIOPHOSPHORODICHLORIDATES AND O-
(4-NITROPHENYL)THIOPHOSPHOROCHLORIDATES, Phosphorus, Sulfur, and Silicon and the Related
Elements, 114:1-4, 123-127, DOI: 10.1080/10426509608046418
To link to this article: http://dx.doi.org/10.1080/10426509608046418
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