Photo-induced aromatic assembly of benzocycloalka[1,2-b] furan and spiro[furan-2(3H),1′-benzocycloalkane] derivatives

Tetrahedron Letters

Volumn 46, Issue 43, 2005, Pages 7303-7306

  Fujino, Reika ^a   Kajikawa, Shougo ^a   Nishino, Hiroshi ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

Aromatic assembly; Benzannulation; Dihydrophenalenes; Hydrohelicenes; Photoreaction

Indexed keywords

CYCLOALKANE DERIVATIVE; FURAN DERIVATIVE; XANTHENE DERIVATIVE;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; PHOTOREACTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 25444449553     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.134     Document Type: Article

References (23)

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14. The benzocyclopenta[1,2-b]furan (1a ) or spirofuran 3a (0.2 mmol) was added to a mixture of acetonitrile (9 mL) and 2 M hydrochloric acid (1 mL) in a 10 mL quartz irradiation tube previously purged with argon for a period of 1 min. The tube was sealed with a glass stopper. The solution was then irradiated by a 100 W high-pressure mercury lamp (Eikohsha EHB-WI-100 lamp) for 6 h using a merry-go-round apparatus. After the irradiation, the mixture was extracted with dichloromethane and the obtained products were separated by silica gel TLC (Wakogel B-10) with diethyl ether-hexane (2:8 v/v) as the developing solvent. The analytical sample was further purified by recrystallization from ethanol.
15. 16O: C, 88.20; H, 5.92. Found: C, 88.40; H, 5.92.
16. 16O: C, 85.68; H, 7.19. Found: C, 85.58; H, 7.30.
17. The X-ray crystallographic data of 3i, 4d′, and 4i have been deposited as supplementary publication numbers CCDC249342, CCDC251416, and CCDC251415, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ].
18. The blank experiment of 3h was conducted in the same reaction media for 36 h in the dark to afford 3g in only 9% yield.
19. The heats of formations for 3g and 3h were revealed to be -21.7 and -22.7 kcal/mol, respectively, based on the PM3 calculations. The PM3 calculations were performed by CAChe Work System version 4.9.3.
20. 3 = Ph), according to the PM3 calculation.
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