20117-76-4Relevant academic research and scientific papers
Diastereospecific Hydroxyiodination of 1-Acetoxycyclohex-2-ene via Intramolecular Delivery of Oxygen
Bange, Johannes,Haughan, Alan F.,Sweeney, J. B.
, p. 1405 - 1408 (1994)
The previously unreported reaction of N-iodosuccinimide with acetoxycyclohex-2-ene to give monoacetates of 3-iodocyclohexane-1,2-diols is diastereospecific.
Hydroxyhalogenations of acyloxycyclohex-2-enes. Part 3. Iterative 1,2-hydroxyiodination of acetoxycyclohex-2-ene: Preparation of tetraacetyl conduritol D
Bange, Johannes,Haughan, Alan F.,Knight,Sweeney, Joseph
, p. 1039 - 1046 (2007/10/03)
Compound 22, the tetraacetyl derivative of conduritol D, has been synthesized by repeated hydroxyiodination reactions in nine steps from acetoxycyclohex-2-ene.
REACTION OF 1,3-CYCLOHEXADIENE WITH THE ACETIC ACID-ACETIC ANHYDRIDE SYSTEM INITIATED BY MANGANESE(III) ACETATE
Melikyan, G. G.,Aslanyan, G. Kh.,Panosyan, G. A.,Kazaryan, P. I.,Badanyan, Sh. O.
, p. 222 - 226 (2007/10/02)
The reaction of 1,3-cyclohexadiene with the acetic acid-acetic anhydride system in the presence of manganese(III) acetate was studied.The reaction products were a mixture of the stereoisomers of 2-acetoxy-3-cyclohexenyl- and 4-acetoxy-2-cyclohexenylacetic acid and also 3,4- and 3,6-diacetoxy-1-cyclohexene.The mixture of acetoxy acids was converted into the corresponding hydroxy acids, and the diacetoxycyclohexenes were converted into the corresponding saturated esters.The cis-lactone was obtained as the only reaction product from the mixture of stereoisomersof the γ- and ε-hydroxy acids, while the methyl esters were obtained from the ε-hydroxy acids.
Catalytic One-Pot Osmylation of Cyclohexadienes: Stereochemical and Conformational Studies of the Resulting Polyols
Tschamber, Theophile,Backenstrass, Frederique,Fritz, Hans,Streith, Jacques
, p. 1052 - 1060 (2007/10/02)
Catalytic double osmylation is described for a series of cyclohexadienes in acetone/H2O in the presence of the co-oxidant N-methylmorpholine N-oxide (NMO).The formation of polyols occurred stereospecifically with cyclohexadienes 3, 7, and 11a, leading thereby to tetrols 5a, and 9a and to allo-inositol (14a), respectively.To the contrary, trans-cyclohexadiene-diol 15a gave a mixture of the stereoisomeric inositols 18a (epi), 19a (neo), and 20a (chiro).High-field NMR let to clearcut conformational analyses of the polyhydroxylated derivatives.
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.
DIACETOXYLATION OF CONJUGATED DIENES WITH THALLIUM(III) ACETATE IN ACETIC ACID
Uemura, Sakae,Miyoshi, Haruo,Tabata, Akira,Okano, Masaya
, p. 291 - 295 (2007/10/02)
The reaction of conjugated dienes such as 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, 2,5-dimethyl-2,4-hexadiene, 1,3-cyclopentadiene, and 1,3-cyclohexadiene with thallium(III) acetate in acetic acid at 10-65 deg C for 0.5-15 hr affords an isomeric mixture of the corresponding diacetoxyalkenes (1,2- and 1,4-addition products) in 10-92 percent yields.The 1,2-addition products are predominantly formed in all cases examined except the case of 1,3-cyclopentadiene.The reaction is assumed to proceed through acetoxythallation and dethallation steps, the latter step being accompanied and/or followed by an attack of acetoxyl group.An initial attack of thallium moiety is proposed to occur mainly at C-1 and C-2 carbons in the cases of linear terminal dienes and cyclic dienes, respectively.
