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Titolo:
[2+2]photocycloaddition of 2-(dibenzylamino)ethyl 3-benzoylacrylate in a crystalline state: weak intermolecular interactions as important factors determining efficiency of the solid-state photoreaction
Autore:
Hasegawa, T; Ikeda, K; Yamazaki, Y;
Indirizzi:
Tokyo Gakugei Univ, Dept Chem, Tokyo 1848501, Japan Tokyo Gakugei Univ Tokyo Japan 1848501 , Dept Chem, Tokyo 1848501, Japan
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 22, , anno: 2001,
pagine: 3025 - 3028
SICI:
1472-7781(2001):22<3025:[O23IA>2.0.ZU;2-5
Fonte:
ISI
Lingua:
ENG
Soggetto:
CH/PI INTERACTION; ORGANIC-COMPOUNDS; DATABASE; PHOTODIMERIZATION; COMPLEXES; FACE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
46
Recensione:
Indirizzi per estratti:
Indirizzo: Hasegawa, T Tokyo Gakugei Univ, Dept Chem, 4-1-1 Nukuikitamachi, Tokyo 1848501, Japan Tokyo Gakugei Univ 4-1-1 Nukuikitamachi Tokyo Japan 1848501 n
Citazione:
T. Hasegawa et al., "[2+2]photocycloaddition of 2-(dibenzylamino)ethyl 3-benzoylacrylate in a crystalline state: weak intermolecular interactions as important factors determining efficiency of the solid-state photoreaction", J CHEM S P1, (22), 2001, pp. 3025-3028

Abstract

Upon UV irradiation 2-(dibenzylamino)ethyl 3-benzoylacrylate in a crystalline state undergoes efficient [2+2] photocycloaddition to give a head-to-tail dimer, bis[2-(dibenzylamino)ethyl] c-2,t-4-dibenzoylcyclobutane-r-1,t-3-dicarboxylate, quantitatively. The X-ray structure analysis shows CH/pi interactions between aliphatic and aromatic C-H bonds and benzene rings make the orientation of the benzoylacrylate molecules in a crystalline state suitable for the [2+2] photocycloaddition. The aliphatic CH/pi interaction is responsible for formation of the cis-configuration between the 2-( dibenzylamino) ethoxycarbonyl and benzoyl groups in the cyclobutanedicarboxylate. The cyclobutanedicarboxylate is hydrolyzed quantitatively to 2,4-dibenzoylcyclobutane-1,3-dicarboxylic acid, which is not directly produced from irradiation of crystals of 3-benzoylacrylic acid.

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Documento generato il 31/03/20 alle ore 19:36:53