92115-30-5Relevant academic research and scientific papers
Clemmensen Reduction. X. The Synthesis and Acidolysis of Some Aryl Alkyl Substituted Cyclopropane-1,2-diols
Davis, Brian R.,Hinds, Mark G.,Ting, Philip P. C.
, p. 865 - 875 (2007/10/02)
The synthesis of a number of 1-alkyl-2-arylcyclopropane-1,2-diols is reported.Reductive treatment of suitably substituted 1,3-diketones gave a cyclopropanediyl diacetate from which the diol was obtained.Reaction of these diols with acid gave α-hydroxy ketones, in which an alkyl group, rather than an aryl group, was adjacent to the carbonyl function.Clemmensen reduction of the 1,3-diketones gave products of rearrangement, generally similar to those obtained by acidolysis of the cyclopropane-1,2-diols.The relationship of these results to thermochemical studies on the stability of carboxonium ions is discussed.
PHOTOCHEMICAL REACTION OF PHENYL-SUBSTITUTED 1,3-DIKETONES.
Yoshioka,Suzuki,Oka
, p. 1604 - 1607 (2007/10/02)
Irradiation of 2,2-dimethyl-1-phenyl-1,3-diketones with 3-ethyl or 3-isopropyl substituents gave type II cyclization product, 3-hydroxy-2,2,4-trimethyl-3-phenylcyclobutanone or 3-hydroxy-2,2,4,4-tetramethyl-3-phenylcyclobutanone, along with type I cleavage products. The type II cyclization/type I cleavage ratio is greater with a 3-isopropyl group than with a 3-ethyl group. A similar irradiation of 2,2-dimethyl-1-phenyl-1,3-butanedione gave type I cleavage products and no type II cyclization product. Irradiation of 2,4-dimethyl-1-phenyl-1,3-pentanedione gave 3-hydroxy-2,2,4-trimethyl-3-phenylcyclobutanone and propiophenone.
