Literature DB >> 17165904

Intramolecular ene reaction of 1,6-fullerenynes: a new synthesis of allenes.

Margarita Altable1, Salvatore Filippone, Angel Martín-Domenech, Mireia Güell, Miquel Solà, Nazario Martín.   

Abstract

[Structure: see text] Thermal treatment of 1,6-fullerenynes bearing an alkyl group on the terminal carbon of the alkyne moiety leads quantitatively to new allenes through a reaction mechanism involving an intramolecular ene process. This reaction outcome is in contrast to that recently found for free terminal alkynes which form cyclobutene derivatives through a [2+2] cyclization mechanism.

Entities:  

Year:  2006        PMID: 17165904     DOI: 10.1021/ol062353u

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Formal [2 + 2 + 2] cycloaddition strategy based on an intramolecular propargylic ene reaction/Diels-Alder cycloaddition cascade.

Authors:  Julia M Robinson; Takeo Sakai; Katsuhiko Okano; Takafumi Kitawaki; Rick L Danheiser
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

2.  Cyano Diels-Alder and cyano ene reactions. Applications in a formal [2 + 2 + 2] cycloaddition strategy for the synthesis of pyridines.

Authors:  Takeo Sakai; Rick L Danheiser
Journal:  J Am Chem Soc       Date:  2010-09-29       Impact factor: 15.419

3.  Why nature eschews the concerted [2 + 2 + 2] cycloaddition of a nonconjugated cyanodiyne. Computational study of a pyridine synthesis involving an ene-Diels-Alder-bimolecular hydrogen-transfer mechanism.

Authors:  Yu Lan; Rick L Danheiser; K N Houk
Journal:  J Org Chem       Date:  2012-01-25       Impact factor: 4.354

  3 in total

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