Conformational Behaviour of Medium-sized Rings. Part 10. Dithiosalicylides and Trithiosalicylides

DOI: 10.1039/P19820001637

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1637 - 1648 (1982)

Update date:2022-08-05

Topics:

Authors:

Guise, G. Bruce

Ollis, W. David

Peacock, Judith A.

Stephanatou, Julia Stephanidou

Stoddart, J. Fraser

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19820001637

The trithiosalicylide derivatives (8)-(11) have been synthesised and shown by temperature-dependent 1H n.m.r. spectroscopy to exist in solution as ring inverting (35a)<*>(35b) enantiomeric helical conformations with trans-thioester linkages.The free energies of activation for these conformational changes are ca. 10 kcal mol^-1 higher than those for the similar process in the corresponding trisalicylides.In contrast with the trisalicylides, the trithiosalicylides can only ring invert between enantiomeric helical conformations via intermediates containing a cis-thioester linkage.The dithiosalicylide derivatives (3)-(7) have been synthesised; the temperature dependence of the 1H n.m.r. spectrum of di-o-thiothymotide (7) has been interpreted in terms of ring inversion (40a)<*>(40b) between enantiomeric boat conformations.Comparison of the ΔG^<*> value of 24.6 kcal mol^-1 for this conformational change with that of 17.7 kcal mol^-1 previously obtained for di-o-thymotide (41) suggests that cis-thioester linkages are subject to more resonance stabilisation than are cis-ester linkages.

Full text of DOI:10.1039/P19820001637

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:3,6-dimethyl-2-mercaptobenzoic acid

Cas No:77149-12-3

R&D Labs maybe for 77149-12-3

TIANJIN ZHONGXIN CHEMTECH CO.,LTD.

Contact:86-022-66880623

Address:FINANCIAL STREET WEST BLK 7, #308, NO.52 XINCHENG WEST ROAD, TEDA, TIANJIN, P.R.CHINA
Zhengzhou Yuanli Biological Technology Co., Ltd.

Contact:+86-371-67897870/67897895

Address:No. 38, Qingyang Street, Zhengzhou, Henan, China
Hunan Hui Bai Shi（YUNBANG）Biological Technology Co.,Ltd

website:http://www.hunanyunbang.com/

Contact:+86-731-85525605/+86-13319518603

Address:1103,C3 Building,No.27 Wenxuan Road, Yuelu District
SHIJIAZHUANG CHENSHI IMPORT AND EXPORT CO.,LTD

Contact:+86-311-89871056

Address:RM2017 BUILDING CTIANSHAN GALAXY PLAZA,NO168 CHANGJIANG ROAD,GAOXIN DISTRICT,SHIJIAZHUANG CITY, HEBEI,CHINA
Shreeji pharma international

Contact:0091-265-2313036

Address:311, ATLANTIS HEIGHTS SARABHAI MAIN ROAD,VADIWADI ,VADODARA

Relevant to this article

Reaction of Halomethyl Ketones with Thiols and Selenols: Substitution vs. Reduction

Doi:10.1021/jo00325a038
(1981)
Enantioselective synthesis of thiosulfinates and of acyclic alkylidenemethylene sulfide sulfoxides

Doi:10.1002/ejoc.200400892
(2005)
Lewis acid-promoted direct synthesis of N-unsubstituted hydrazones via the reaction of hydrazine with acetophenone and isatin derivatives

Doi:10.1134/S1070363216120471
(2016)
Reactivities of Oxalamidines (N,N-Oxalins)

Doi:10.1006/bioo.1995.1017
(1995)
Regioselective isomerisation of highly substituted 1- methylenecyclohexenepoxides to the corresponding allylic alcohols. Influence of the base and of the protecting groups

Doi:10.1007/s00706-003-0153-7
(2004)
A Novel α-Hydroxydihydrochalcone from the Heartwood of Pterocarpus angolensis D.C.: Absolute Configuration, Synthesis, Photochemical Transformations, and Conversion into α-Methyldeoxybenzoins

Doi:10.1039/P19810000263
(1981)

Article Doi