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Synthesis and ring-chain-ring tautomerism of bisoxazolidines, thiazolidinyloxazolidines, and spirothiazolidines

Saiz, C and Wipf, P and Mahler, G (2011) Synthesis and ring-chain-ring tautomerism of bisoxazolidines, thiazolidinyloxazolidines, and spirothiazolidines. Journal of Organic Chemistry, 76 (14). 5738 - 5746. ISSN 0022-3263

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The synthesis of fused heterocycles such as thiazolidinyl-oxazolidine 3 is described starting from Tris·HCl. The mercaptomethyl bisoxazolidine 8 was found to convert to the corresponding thiazolidinyloxazolidine 3 and the spiro-heterocycle 4 by a ring-chain-ring tautomerism, depending on the electronic nature of the ring substituents as well as the reaction conditions. This equilibration pathway is absent in the hydroxymethyl bisoxazolidines 2. Computational studies confirm that both kinetic and thermodynamic control features play a role in the product distribution. © 2011 American Chemical Society.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Saiz, C
Wipf, Ppwipf@pitt.eduPWIPF
Mahler, G
Date: 15 July 2011
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 76
Number: 14
Page Range: 5738 - 5746
DOI or Unique Handle: 10.1021/jo2008498
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Kinetics; Molecular Conformation; Oxazoles--chemical synthesis; Oxazoles--chemistry; Stereoisomerism; Thermodynamics
Other ID: NLM NIHMS304200, NLM PMC3422676
PubMed Central ID: PMC3422676
PubMed ID: 21634420
Date Deposited: 18 Jul 2014 21:17
Last Modified: 02 Feb 2019 15:57


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