Ulbricht, Mathias; Thurner, Joern Uwe; Siegmund, Manfred; Tomaschewski, Georg:

Photochemical Wolff-rearrangement of cyclic 2-diazo-1,3-dicarbonyl compounds.

In: Zeitschrift fuer Chemie (Z.Chem.), Jg. 28 (1988) ; Nr. 3, S. 102-103
ISSN: 0044-2402
Zeitschriftenaufsatz / Fach: Chemie
The photochem. Wolff-rearrangement of title compds. I (X = CH2CHPhCH2, CH2CMe2CH2, CHPhCHPhCH2, OCMe2O, NRCONR; R = Me, Ph, cyclohexyl) at 120K-200nm gave ketoketenes II which on warning above 180K gave cyclopantanone and ketene dimers in some cases. Photolysis of I (X = NPhCONPh) in alc. at 300K-300nm gave valance isomer diazirine III. Photolysis of I (X = CH2CHPhCH2) in EtOH at 300K-200nm gave Et 4-phenylcyclopentan-2-onecarboxylate whereas photolysis of I (X = NPhCONPh) in MeOH at 300K-200nm gave Me 1,3-diphenylhydantoincarboxylate.