Literature DB >> 16390113

Challenge to detect 1,4-zwitterions spectroscopically in a ketene-alkene reaction.

Takahisa Machiguchi1, Junko Okamoto, Yumiko Morita, Toshio Hasegawa, Shinichi Yamabe, Tsutomu Minato.   

Abstract

The first example of direct spectroscopic detection of transient species, 1,4-zwitterions, generated in a ketene-alkene reaction is reported. Also, a striking result of the intervention of an unprecedented "1,4-zwitterion neutral dimer" is presented in a new mechanistic pathway; the ketene-alkene reaction gives the product cyclobutanone from the initial cycloadduct alpha-methyleneoxetane.

Entities:  

Year:  2006        PMID： 16390113     DOI： 10.1021/ja054619i

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  3 in total

1.  Pericyclic cascade with chirality transfer: reaction pathway and origin of enantioselectivity of the hetero-Claisen approach to oxindoles.

Authors:  Nihan Çelebi-Ölçüm; Yu-hong Lam; Edward Richmond; Kenneth B Ling; Andrew D Smith; Kendall N Houk
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-04       Impact factor: 15.336

2.  Acid catalyzed cyclodimerization of 2,2-bis(trifluoromethyl)-4-alkoxy-oxetanes and -thietanes. Synthesis of 2,2,6,6-tetrakis(trifluoromethyl)-4,8-dialkoxy-1,5-dioxocanes and 3,3,7,7-tetrakis(trifluoromethyl)-9-oxa-2,6-dithia-bicyclo[3.3.1]nonane.

Authors:  Viacheslav A Petrov; Will Marshall
Journal:  Beilstein J Org Chem       Date:  2010-05-10       Impact factor: 2.883

3.  Synthesis of 1,5-Dioxocanes via the Two-Fold C-O Bond Forming Nucleophilic 4+4-Cyclodimerization of Cycloprop-2-en-1-ylmethanols.

Authors:  Andrew Edwards; Trevor Bennin; Marina Rubina; Michael Rubin
Journal:  RSC Adv       Date:  2015-08-19       Impact factor: 3.361
  3 in total

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