85288-61-5Relevant academic research and scientific papers
Synthesis of 3-methyl-2-cyclohexenones catalyzed by mercury(II) salts and their microwave assisted BiCl3 catalyzed aldol condensations
Zhang, Chen,Wang, Bi-Song,Chen, Shi-Feng,Zhang, Shao-Qiao,Cui, Dong-Mei
experimental part, p. 165 - 169 (2011/02/17)
HgSO4 catalyzed hydrative cyclization of 1,6-heptadiynes is present. This reaction proceeded smoothly under the mild condition for differently 4-sustituted 1,6-diynic substrates giving corresponding 3-methyl-2-cyclohexenones with high to excell
RULES FOR RING CLOSURE: APPLICATION TO INTRAMOLECULAR ALDOL CONDENSATIONS IN POLYKETONIC SUBSTRATES
Baldwin, Jack E.,Lusch, Michael J.
, p. 2939 - 2947 (2007/10/02)
An extension of the nomenclature for classifying ring closures to include intramolecular reactions of enolate anions is described, and the rules governing such cyclizations are enumerated.The syntheses of the polyketonic substrates 4-acetyl-2,6-heptanedione (11), 4-acetyl-4-methyl-2,7-octanedione (24), and 3-acetyl-3-methyl-1,6-diphenyl-1,6-heptanedione (33) were carried out, and their base-induced intramolecular aldol condensations studied.With each substrate a favored 6-(enolendo)-exo-trig cyclization to produce cyclohexenone products was the only ring forming reaction observed, this process predominating in all instances over competing disfavored 5-(enolendo)exo-trig closures, and also over other competing favored cyclizations.The identity of the cyclization product 12 derived from 11 was confirmed by aromatizing 12 to 17, and alternately synthesizing 17 from 3-bromo-5-methylphenol.
