Cyclic β-hydroxy-α-nitrosulfone isomers readily interconvert <i>via</i> open-chain aldehyde forms-Reference-Cited by-同舟云学术

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Cyclic β-hydroxy-α-nitrosulfone isomers readily interconvert via open-chain aldehyde forms

Published:2023 Issue:24 Volume:21 Page:5033-5039
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Wade Peter A.¹^ORCID,Tandon Ruchi¹,Carroll Patrick J.²

Affiliation:

1. Department of Chemistry, Drexel University, Philadelphia, PA 19104, USA

2. Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, USA

Abstract

Cyclic β-hydroxy-α-nitrosulfones isomerize under exceptionally mild conditions. For a cyclic β,β-dihydroxy-α-nitrosulfone, simple isomerization competes with hemiacetal formation.

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/OB/D3OB00349C

Reference13 articles.

1. R. S.Shallenberger , Advanced Sugar Chemistry , AVI , 1982 , pp. 70–111

2. P. A.Wade and R. M.Giuliano , Nitro Compounds. Recent Advances in Synthesis and Chemistry , ed. H. Feuer and A. T. Nielsen , VCH , 1990 , pp. 141–147

3. Reactions of (1-nitroethenyl)sulfonylbenzene, a nitroethene derivative geminally substituted by a second W-group

4. E. L.Eliel and S. H.Wilen , Stereochemistry of Organic Compounds AR , Wiley , 1994 , p. 696

5. Enthalpic and Entropic Contributions to the Conformational Free Energies of Methylthio, Methylsulfinyl, Methylsulfonyl, Phenylthio, Phenylsulfinyl, and Phenylsulfonyl [S(O)nR, n = 0, 1, 2; R = CH3, Ph] Groups in Cyclohexane

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