77202-47-2Relevant academic research and scientific papers
PdI2-catalyzed regioselective cyclocarbonylation of 2-allyl phenols to dihydrocoumarins
Amzquita-Valencia, Manuel,Alper, Howard
, p. 5827 - 5829 (2015/01/08)
A simple, efficient, and regioselective synthesis of 3-methyl-3,4-dihydrocoumarins is reported. The reaction of 2-allyl phenols with synthesis gas was catalyzed by PdI2, and 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (L1) and 1,3,5,7-tetramethyl-6-tetradecyl-2,4,8-trioxa-6-phosphaadamantane (L2) were effective as ligands, affording good product selectivity in all cases.
Reactions of 2-phenyl-4H-1,3,2-benzodioxaborin, a stable ortho-quinone methide precursor
Chambers, Jeffrey D.,Crawford, Jason,Williams, Haydn W. R.,Dufresne, Claude,Scheigetz, John,et al.
, p. 1717 - 1732 (2007/10/02)
Thermolysis of 1-phenyl-4H-1,3,2-benzodioxaborins generated the corresponding ortho-quinone methides, which were found to undergo intermolecular cycloaddition reactions with ethyl vinyl ether, dihydropyran, β-methylstyrene, cyclohexene, and 1-ethoxy-1-trimethylsiloxy-1-propenes to give various substituted chromans.Intramolecular trapping of the quinone methides with an olefin led to the syntheses of several analogs of tetrahydrocannabinols. ortho-Quinone methides, generated by treatment of the 2-phenyl-4H-1,3,2-benzodioxaborins with a Lewis acid, react with various nucleophiles to give the corresponding 1,4-addition products.Thus, alkyl and aryl thiols, alcohols, amine, hydride, allyl trimethylsilane, acetophenone, and diethyl malonate as well as some aryl compounds react with the quinone methide to give various 2-substituted phenols.Intramolecular reaction of the quinone methide with an aryl group led to the preparation of some 4-phenylchromans and tetralins.
