81887-98-1Relevant academic research and scientific papers
SYNTHESIS AND PROPERTIES OF 2-DIAZO-1,3-DICARBONYL COMPOUNDS. V. SYNTHESIS AND 1,2-NUCLEOPHILIC REARRANGEMENTS OF SOME 2-DIAZO-3-HYDROXY-1-CYCLOHEXANONES
Nikolaev, V. A.,Zhdanova, O. V.,Korobitsyna, I. K.
, p. 488 - 498 (2007/10/02)
2-Diazo-3-hydroxy, 2-diazo-3-hydroxy-5,5-dimethyl, and 2-diazo-3-hydroxy-4,4,6,6-tetramethyl-1-cyclohexanones were obtained by reduction of 2-diazo 1,3-diketones of the cyclohexane series, and their spectral characteristics were determined.Photolytic, catalytic, and thermal elimination of nitrogen in these diazo compounds is only accompanied by 1,2-nucleophilic rearrangements.During photolysis of the diazohydroxycyclohexanones in an aqueous medium the main reaction path is a Wolff rearrangement, i.e., ring contraction with the formation of hydroxy and unsaturated acids of the cyclopentane series and some of their derivatives.Acid decomposition of the diazohydroxycyclohexanones leads mainly to an alkyl shift as a result of which (hydroxymethylene)cyclopentanones are formed with ring contraction.
