63559-21-7Relevant articles and documents
Rhodium-catalyzed asymmetric cyclodimerization of oxabenzonorbornadienes and azabenzonorbornadienes: Scope and limitations
Allen, Anna,Le Marquand, Paul,Burton, Ryan,Villeneuve, Karine,Tam, William
, p. 7849 - 7857 (2008/02/12)
(Chemical Equation Presented) Cationic rhodium(I)-catalyzed cyclodimerization of oxabenzonorbornadienes produced naphtho[1,2-b]-furan ring systems in a single step with excellent yields and excellent enantioselectivities. The effect of various Rh(I) catalysts, Ag(I) salts, solvents, and phosphine ligands on the yield and enantioselectivity of the reaction was investigated, and the scope and limitations of this reaction with various oxabicyclic alkenes were studied. Similar results were obtained with the azabenzonorbornadiene analogues, providing the corresponding cyclodimerization products in excellent yields and excellent enantioselectivities.
Syntheses of Highly Substituted Benzenes via Diels-Alder Reactions with 2H-Pyran-2-ones
Ziegler, Thomas,Layh, Marcus,Effenberger, Franz
, p. 1347 - 1356 (2007/10/02)
The 2H-pyran-2-ones (α-pyrones) 1 react as dienes in Diels-Alder reactions with acetylene derivatives.The primarely formed cycloadducts immediately aromatize to benzenes by CO2 elimination.Thus, methyl acetylenedicarboxylate (2a) gives dimethyl phthalates 3, and methyl acetylenediphosphonate (2b) gives dimethyl 1,2-phenylenediphosphonates 8.The reactions of 1-(dimethylamino)-1-methoxyethene (9) with 1 regioselectively produce N,N-dimethylanilines 10 and isomeric homophthalate derivatives 12.Naphthoquinones 14 could be generated from 1,4-benzoquinone (13) and 1 in the presence of acetic anhydride and Pd/C.Hydroxy-2H-pyran-2-ones 4 react via their trimethylsilyl ether 6 analogously with 2a to give dimethyl (trimethylsiloxy)phthalates 7 which are easily converted to phenols 5 by acid-catalyzed hydrolysis.