83766-83-0Relevant academic research and scientific papers
Birch Reductive Alkylation of Methyl m-(Hydroxymethyl)benzoate Derivatives and the Behavior of o- and p-(Hydroxymethyl)benzoates under Reductive Alkylation Conditions
Fretz, Samuel J.,Hadad, Christopher M.,Hart, David J.,Vyas, Shubham,Yang, Dexi
supporting information, p. 83 - 92 (2013/03/29)
Birch reductive alkylation of methyl m-(hydroxymethyl)benzoate derivatives, using lithium in ammonia-tetrahydrofuran in the presence of tertbutyl alcohol, can be achieved without significant loss of benzylic oxygen substituents. Similar treatment of o- and p-(hydroxymethyl)benzoate derivatives results largely in loss of benzylic oxygen substituents. The results are rationalized by computations describing electron density patterns in the putative radical anion intermediate involved in these reactions.
Photochemical and Acid-Catalyzed Dienone-Phenol Rearrangements. The Effect of Substitutents on the Regioselectivity of 1,4-Sigmatropic Rearrangements of the Type A Intermediate
Schultz, Arthur G.,Hardinger, Steven A.
, p. 1105 - 1111 (2007/10/02)
Birch reduction of isophthalic acid and 3-cyanobenzoic acid followed by (1) methylation of the resulting enolate with methyl iodide and (2) esterification with diazomethane proved 2-carbomethoxy- and 2-cyano-6-methyl-6-carbomethoxy-1,4-cyclohexadienes 9 and 25.Type A photorearrangement of a series of 2-carbomethoxy-, 2-cyano-, 2-methoxy-, and 2-methyl-4-carbomethoxy-4-methyl-2,5-cyclohexadien-1-ones 11, 26, 45a, and 45b gave 4-carbomethoxy-3-methyl-2-substituted-phenols 12, 28, 46, and 31.It has been demonstrated that the regioselectivity of type A photorearrangement of C(2) substituted 2,5-cyclohexadien-1-ones is governed by electronic rather than steric effects to give the intermediate C(1) rather than C(3) substituted bicyclo1,5>hex-3-en-2-ones.Regioselectivities of the acid-catalyzed dienone-phenol rearrangements of C(2) substituted 2,5-cyclohexadienones 11, 45a, and 45b appear to be dependent upon the relative stabilities of carbocations resulting from migration of the C(4) carbomethoxy group.
CHEMOSELECTIVE INTRAMOLECULAR NITRONE-OLEFIN CYCLOADDITION : AN EFFICIENT ROUTE TO FUNCTIONALIZED CIS HYDRINDANE SYSTEMS
Stanssens, Dirk,Keukeleire, Denis De,Vandewale, Maurits
, p. 813 - 820 (2007/10/02)
Isoxazolidines 5a-c and 8 were obtained via chemoselective nitrone-olefin cycloaddition in suitably modified 1,4-cyclohexadienes 1a-c; 5a and 5c were transformed to highly functionalized cis-hydrindanes.
