Stereoselective 1,3-Dipolar Cycloaddition of a Nitrile Ylide Photochemically Generated from 2,3-Diphenyl-2H-azirine to Substituted Methylene Lactones

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Title:Stereoselective 1,3-Dipolar Cycloaddition of a Nitrile Ylide Photochemically Generated from 2,3-Diphenyl-2H-azirine to Substituted Methylene Lactones
Creators:
Častulík, Jakub
Jonas, Jaroslav
Mazal, Ctibor
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 5, pp. 708-716
Uncontrolled Keywords:Methylene lactones, X-Ray diffraction, Spiro compounds, Nitrile ylide, Photoisomerizations, Dipolar cycloadditions, NMR spectroscopy

Abstract

The nitrile ylide photochemically generated from 2,3-diphenyl-2<i>H</i>-azirine adds to both isomers of 3-(tosyloxymethylene)tetrahydrofuran-2-one with excellent regio- and stereoselectivity giving spiroheterocyclic products in moderate yields. X-Ray structure determination showed dibutolactone to have the <i>E</i>-configuration; the corresponding <i>Z</i>-isomer was prepared photochemically. <p>

Title:Stereoselective 1,3-Dipolar Cycloaddition of a Nitrile Ylide Photochemically Generated from 2,3-Diphenyl-2H-azirine to Substituted Methylene Lactones
Creators:
Častulík, Jakub
Jonas, Jaroslav
Mazal, Ctibor
Uncontrolled Keywords:Methylene lactones, X-Ray diffraction, Spiro compounds, Nitrile ylide, Photoisomerizations, Dipolar cycloadditions, NMR spectroscopy
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:5
Page Range:pp. 708-716
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000708UNSPECIFIED
ID Code:1673
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Častulík, Jakub; Jonas, Jaroslav; Mazal, Ctibor (2000) Stereoselective 1,3-Dipolar Cycloaddition of a Nitrile Ylide Photochemically Generated from 2,3-Diphenyl-2H-azirine to Substituted Methylene Lactones. Collection of Czechoslovak Chemical Communications, 65 (5). pp. 708-716. ISSN 0010-0765

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