5682-62-2Relevant academic research and scientific papers
Light-induced geometric isomerization of 1,2-diphenylcyclopropanes included within Y zeolites: Role of Cation-guest binding
Kaanumalle, Lakshmi S.,Sivaguru,Sunoj,Lakshminarasimhan,Chandrasekhar,Ramamurthy
, p. 8711 - 8720 (2007/10/03)
Through a systematic study of several diphenylcyclopropane derivatives, we have inferred that the cations present within a zeolite control the excited-state chemistry of these systems. In the parent 1,2-diphenylcylopropane, the cation binds to the two phenyl rings in a sandwich-type arrangement, and such a mode of binding prevents cis-to-trans isomerization. Once an ester or amide group is introduced into the system (derivatives of 2β,3β-diphenylcyclopropane-1α-carboxylic acid), the cation binds to the carbonyl group present in these chromophores and such a binding has no influence on the cis-trans isomerization process. Cation-reactant structures computed at density functional theory level have been very valuable in rationalizing the observed photochemical behavior of diphenylcyclopropane derivatives included in zeolites. While the parent system, 1,2-diphenylcylopropane, has been extensively investigated in the context of chiral induction in solution, owing to its failure to isomerize from cis to trans, the same could not be investigated in zeolites. However, esters of 2β,3β-diphenylcyclopropane-1α-carboxylic acid could be studied within zeolites in the context of chiral induction. Chiral induction as high 20% ee and 55% de has been obtained with selected systems. These numbers, although low, are much higher than what has been obtained in solution with the same system or with the parent system by other investigators (maximum ～10% ee).
Enantio- and diastereodifferentiating cis,trans-photoisomerization of 2β,3β-diphenylcyclopropane-1α-carboxylic acid derivatives in organized media
Cheung, Eugene,Chong, Kenneth C. W.,Jayaraman, Sivaguru,Ramamurthy,Scheffer, John R.,Trotter, James
, p. 2801 - 2804 (2007/10/03)
Four methods of asymmetric induction in the cis,trans-photoisomerization of 2β,3β-diphenylcyclopropane-1α-carboxylic acid derivatives were studied. Best results (ca. 80% de) were obtained by irradiation of chiral esters, amides, and salts in NaY and LiY z
STEREOCHEMISTRY OF THE ADDITION OF CHLORINE TO METHYL 2,3-DIPHENYL-2-CYCLOPROPENECARBOXYLATE
Grigorova, T. N.,Komendantov, M. I.
, p. 265 - 267 (2007/10/02)
The reaction of chlorine with methyl 2,3-diphenyl-2-cyclopropenecarboxylate was investigated.The addition of chlorine to the cyclopropene double bond takes place stereospecifically at the cis position.The structure and configuration of the obtained methyl
Reaction of HCo(CO)4 with Methyl 2,3-Diphenyl-2-cyclopropene-1-carboxylate: Synthesis of Methyl t,t-2,3-Diphenyl-c-2-formylcyclopropane-r-1-carboxylate
Nalesnik, Theodore E.,Fish, John G.,Horgan, Steven W.,Orchin, Milton
, p. 1987 - 1990 (2007/10/02)
Reaction of HCo(CO)4 with the diphenylcyclopropene 1 leads to the three possible hydrogenated cyclopropanes but in addition a single hydroformylation product is formed.This aldehyde was synthesized by an unambiguous procedure; it is compound 2, formed by
