Literature DB >> 19921003

Synthesis and rearrangement of a bridged thioamide.

Michal Szostak1, Jeffrey Aubé.   

Abstract

The synthesis of a bridged thiolactam is described. This thiolactam is shown to undergo an unusual C-N bond cleavage reaction under conditions of its synthesis. Spectroscopic properties of the thiolactam indicate a considerable degree of twist of the thioamide bond.

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Year:  2009        PMID： 19921003     DOI： 10.1039/b917508c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  5 in total

1.  Structural characterization of N-protonated amides: regioselective N-activation of medium-bridged twisted lactams.

Authors:  Michal Szostak; Lei Yao; Victor W Day; Douglas R Powell; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

Review 2.  Chemistry of bridged lactams and related heterocycles.

Authors:  Michal Szostak; Jeffrey Aubé
Journal:  Chem Rev       Date:  2013-06-17       Impact factor: 60.622

3.  An efficient computational model to predict protonation at the amide nitrogen and reactivity along the C-N rotational pathway.

Authors:  Roman Szostak; Jeffrey Aubé; Michal Szostak
Journal:  Chem Commun (Camb)       Date:  2015-04-14       Impact factor: 6.222

4.  Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

5.  Resonance promoted ring-opening metathesis polymerization of twisted amides.

Authors:  Mizhi Xu; Krista K Bullard; Aja M Nicely; Will R Gutekunst
Journal:  Chem Sci       Date:  2019-08-30       Impact factor: 9.825
  5 in total

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