56532-18-4Relevant academic research and scientific papers
Substituent Effects on Hydrogenation of Aromatic Rings: Hydrogenation vs. Hydrogenolysis in Cyclic Analogues of Benzyl Ethers.
Anzalone, Luigi,Hirsch, Jerry A.
, p. 2128 - 2133 (2007/10/02)
Carbalkoxy substituents are shown to retard the hydrogenation of aromatic rings over Rh/C catalyst.Hydrogenolysis predominates with acyclic (benzyloxy)acetates over this catalyst, but both hydrogenation and hydrogenolysis become sluggish with 2-isochroman-4-ones (1).However, phthalides may be cleanly hydrogenated in moderate to excellent yields without significant hydrogenolysis.Placing a benzyl ether in a ring system appears to greatly retard hydrogenolysis relative to the acyclic analogues.
Stereochemistry of Decarbalkoxylation of Cyclic Geminal Diesters Effected by Water and Lithium Chloride in Me2SO
Krapcho, A. Paul,Weimaster, John F.
, p. 4105 - 4111 (2007/10/02)
The stereochemical consequences of the decarbalkoxylation of cyclic geminal diesters by LiCl-H2O-Me2SO have been examined.The norbornene diester 13 and the norbornane diester 16 lead predominantly to the exoesters 14 and 17, respectively.The 2-methylcyclohexane diester 22 leads to esters containing more cis (23) than trans (24) isomer.The diesters 19,25, and 28 lead to nearly equal amounts of the cis and trans esters.In these latter cases,the enolates generated from the esters (via LDA) are protonated in a nonstereoselective fashion on quenching with water.This is suggestive of an enolate intermediate in the decarbalkoxylation reaction.The implications of these sterochemical results are discussed.
