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ω‐Hydroxy‐ ortho ‐quinodimethane: trapping with trifluoroacetone and photocyclization
Author(s) -
Griesbeck Axel G.,
Stadtmüller Stefan
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260928
Subject(s) - chemistry , hemiacetal , bicyclic molecule , benzaldehyde , aldehyde , trapping , photochemistry , benzene , excited state , medicinal chemistry , organic chemistry , catalysis , ecology , biology , physics , nuclear physics
ω‐Hydroxy‐ ortho ‐quinodimethane ( 2 ), generated by photoenolization of 2‐methylbenzaldehyde ( 1 ) in benzene, is quantitatively trapped with trifluoroacetone to give the bicyclic hemiacetal 6 and the hydroxy aldehyde 7 . A less effective trapping reaction is observed with benzaldehyde with the formation of the bicyclic hemiacetal 5 . The formation of benzocyclobutenol 4 is probable due to a two‐photon process involving electronically excited 2 .