Photoreactions of 1,3-dipolar cycloadducts of mesoionic compounds with buckminsterfullerene

Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals

Volumn 376, Issue , 2002, Pages 219-224

  Kawamura, Yasuhiko ^a   Akaishi, Kazuyuki ^a   Nishiuchi, Masaki ^a   Tsukayama, Masao ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

1,3 dipolar cycloaddition; Extrusion; Fullerene; Mesoionic compound; Photoreaction; Thermogravimetry

Indexed keywords

EXTRUSION; FULLERENES; ORGANIC SOLVENTS; THERMOGRAVIMETRIC ANALYSIS; ULTRAVIOLET SPECTROSCOPY; XENON;

1,3-DIPOLAR CYCLOADDITION; HETEROCYCLIC COMPOUNDS; INTRAMOLECULAR HYDROGEN MIGRATION; MESOIONIC COMPOUND;

PHOTOREACTIVITY;

EID: 11144237643     PISSN: 1058725X     EISSN: None     Source Type: Journal    
DOI: 10.1080/10587250210790     Document Type: Conference Paper

References (6)

1. K. T. Pots, 1,3-Dipolar Cycloaddition Chemistry, ed. by A. Padwa (Wiley, New York, 1984), Vol.2, pp. 1-82.
2. R. Gonzalez, B. W. Knight, 61nd F. Wudl, J. Org. Chem., 59, 7949-7951 (1994).
3. S.-H. Wu, W.-Q. Sun, D.-W. Zhang, L.-H. Shu, H.-M. Wu, J.-F. Xu, and X.-F. Lao, J. Chem. Soc., Perkin 1, 1998, 1733-1738.
4. max (e) 433 nm (780).
5. Calculations were carried out using the MOPAC 94 program contained in the CAChe groupserver program (Release 3.8) available from Fujitsu, Co. or Conflex, Co.
6. Dienophiles tested were maleic anhydride and N-phenylmaleimide, in addition to PT. They reacted with 5 to give the corresponding cycloadducts. But compound 4 reacted only with PT, although reactions of 2 and 3 with all dienophiles proceeded well. The cycloadducts were obtained in >70% yield after flash chromatography and recrystallization in all cases.