ω‐Hydroxy‐ ortho ‐quinodimethane: trapping with trifluoroacetone and photocyclization | Zendy

Griesbeck Axel G. | Zendy; Stadtmüller Stefan | Zendy

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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 .

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