Literature DB >> 15932332

Kinetic isotope effects in the thermal C2-C6 cyclization of enyne-allenes: experimental evidence supports a stepwise mechanism.

Michael Schmittel1, Chandrasekhar Vavilala.   

Abstract

Kinetic isotope effects suggest that the thermal C2-C6 cyclization of enyne-allenes proceeds through a stepwise diradical mechanism. This is even true if steric bulk at the alkyne terminus is large, contrary to theoretical predictions by Engels.

Entities:  

Year:  2005        PMID: 15932332     DOI: 10.1021/jo0504971

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

1.  Synthesis of 5-(2-methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11H-benzo[b]fluorene as 2,2'-disubstituted 1,1'-binaphthyls via benzannulated enyne-allenes.

Authors:  Yu-Hsuan Wang; Joshua F Bailey; Jeffrey L Petersen; Kung K Wang
Journal:  Beilstein J Org Chem       Date:  2011-04-19       Impact factor: 2.883

2.  Solving the puzzling competition of the thermal C(2)-C(6) vs Myers-Saito cyclization of enyne-carbodiimides.

Authors:  Anup Rana; Mehmet Emin Cinar; Debabrata Samanta; Michael Schmittel
Journal:  Beilstein J Org Chem       Date:  2016-01-11       Impact factor: 2.883

3.  A click-based modular approach to introduction of peroxides onto molecules and nanostructures.

Authors:  Alissa Horn; Patrick H Dussault
Journal:  RSC Adv       Date:  2020-12-16       Impact factor: 4.036

  3 in total

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