59055-00-4Relevant articles and documents
Highly regioselective lipase-catalyzed acetylation and hydrolysis of acyclic α,ω-terpenediols and their diacetates
Takabe, Kunihiko,Mase, Nobuyuki,Hisano, Takaya,Yoda, Hidemi
, p. 3267 - 3269 (2007/10/03)
Highly regioselective transformations of the acyclic α,ω-terpenediols and their diacetates to the monoacetates using lipase were accomplished. The acetylation of the α,ω-terpenediols gave regioselectively the ω-monoacetates 3, whereas the α-monoacetates 2 were obtained by hydrolysis of the α,ω-diacetates.
Liquid-phase 1,4-Diacetoxylation of Conjugated Dienes with Tellurium(IV) Oxide and Alkali Metal Halides
Uemura, Sakae,Fukuzawa, Shin-ichi,Patil, Suresh R.,Okano, Masaya
, p. 499 - 504 (2007/10/02)
Oxidation of buta-1,3-diene, isoprene, and 2,3-dimethylbuta-1,3-diene with tellurium(IV) oxide and lithium bromide in acetic acid affords an isomeric mixture of the corresponding diacetoxyalkenes (1,2- and 1,4-addition products).The product yield and selectivity for 1,4-isomers are high when an excess of LiBr is employed (LiBr/TeO2 = 5-10).The reaction also proceeds in the presence of NaBr, KBr, LiCl, HBr, or I2 in the place of LiBr, but both the selectivity for 1,4-isomers and the product yield are lower.The reaction hardly occurs using LiF, LiI, NaCl, Br2, and NH4Br as a halogen source.The reaction proceeds catalytically with respect to TeO2 to some extent when a re-oxidant such as H2O2 or t-BuOOH is used.In the cases of 2,5-dimethylhexa-2,4-diene, cyclopenta-1,3-diene, cyclohexa-1,3-diene, and cyclo-octa-1,3-diene the results are unsatisfactory in either the product yield or the selectivity for 1,4-isomers.Halogeno- and/or acetoxy-telluriation of a diene followed by acetolysis of the produced C-X (X = halogen) and C-Te bonds are proposed as one of the possible reaction pathways.
The Reactions of t-Butoxyl with Unsaturated Hydrocarbons: Structure and Reactivity of Allylic Radicals
Cuthbertson, Matthew J.,Rizzardo, Ezio,Solomon, David H.
, p. 1957 - 1973 (2007/10/02)
A radical trapping technique employing 1,1,3,3-tetramethylisoindolin-2-yloxyl (1) as scavenger has been used to study the reactions of t-butoxy radicals with propene, 2-methylpropene, but-1-ene, (E)- and (Z)-but-2-ene, 3-methylbut-1-ene, buta-1,3-diene and 2-methylbuta-1,3-diene.Relative rates of double bond addition and of allylic hydrogen abstraction have been measured and are discussed, as are the relative stabilities of the products formed.The allylic radicals generated in these systems react with (1) mainly by coupling at the more substituted terminus of the radical ? system.Substituent effects on this regioselectivity may be explained in terms of the electrophilicity of (1).