Stereospecific [2+2] photocycloaddition in a pseudodimeric complex between N-ammoniopropylstyrylpyridine and 18-crown-6-containing styrylpyridine

A quaternary 4-styrylpyridinium salt having the N -ammoniopropyl substituent forms a pseudodimeric head-to-tail complex with neutral 18-crown-6-containing 4-styrylpyridine in MeCN through H-bonding. This complex undergoes stereospecific [2+2] photocycloaddition due to preorganization of the ethylene...

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Bibliographic Details
Published inRussian chemical bulletin Vol. 58; no. 9; pp. 1955 - 1961
Main Authors Vedernikov, A. I., Sazonov, S. K., Kuz’mina, L. G., Howard, J. A. K., Alfimov, M. V., Gromov, S. P.
Format Journal Article
LanguageEnglish
Published Boston Springer US 01.09.2009
Subjects
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Inorganic Chemistry
Organic Chemistry
crown ethers
cyclobutanes
styrylheterocycles
X-ray diffraction study
styryl dyes
ammonium ions
complexation
[2+2] photocycloaddition
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Summary:A quaternary 4-styrylpyridinium salt having the N -ammoniopropyl substituent forms a pseudodimeric head-to-tail complex with neutral 18-crown-6-containing 4-styrylpyridine in MeCN through H-bonding. This complex undergoes stereospecific [2+2] photocycloaddition due to preorganization of the ethylene bonds in the syn -arranged chromophoric fragments of the components. The structure of the rctt -isomer of the cyclobutane derivative obtained was established by NMR spectroscopy and X-ray diffraction analysis.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-009-0267-0