Otrho Photocycloaddition of Substituted 4-Phenoxybut-1-Enes. Identification of Rearranged Photocycloadducts by NMR

0166066 - UCHP-M 20000015 RIV BE eng J - Článek v odborném periodiku
Busson, R. - Schraml, Jan - Seayens, W. - Van der Eycken, E. - De Bruyn, A. - Herdewijn, P. - De Keukeleire, D.
Otrho Photocycloaddition of Substituted 4-Phenoxybut-1-Enes. Identification of Rearranged Photocycloadducts by NMR.
Bulletin des Sociétés Chimiques Belges. Roč. 106, - (1997), s. 671-676. ISSN 0037-9646
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 0.718, rok: 1997

The ortho photocycloadducts, formed on irradiation of 3-tert-butyl-4-phenoxybut-1-ene (1a) and 3-acetoxy-4(4-methoxyphenoxy)but-1-ene (1b) at 254 nm, underwent in situ rearrangement totricyclic structures 4a, 5a, and 5b, 5b1, respectively. Hydra-tion of the vinyl ether function in 5a led to 6a, while a si-milar secondary reaction of 5b afforded 8b. A detailed NMRinvestigation of the rearranged ortho photocycloadducts of both1a and 1b revealed not only the relevant structures, but alsofurnished configurational and conformational details.
Trvalý link: http://hdl.handle.net/11104/0063212