Carbohydrate Research 2003-04-22

Tin(II) chloride catalyzed reactions of diazodiphenylmethane with vicinal diols in an aprotic solvent. The reactions with cis- and trans-1,2-cyclohexanediols and 1,2-propanediol.

Sigthor Petursson

文献索引：Carbohydr. Res. 338(9) , 963-8, (2003)

全文：HTML全文

摘要

The paper reports the tin(II) chloride catalyzed reactions of diazodiphenylmethane with the cis- and trans-1,2-cyclohexanediols and R,S-1,2-propanediol in 1,2-dimethoxyethane and the identification of the monodiphenylmethyl ethers formed. The catalyst is shown to work for both the cis- and trans-cyclohexanediols, but the catalyst is unstable at high reagent concentrations, especially in the case of the trans-isomer. Conditions where catalyst destruction is negligible show that the rate of the reaction with the trans-isomer is larger than with the cis-isomer. The reactions with 1,2-propanediol show small difference between the selectivity for the primary and secondary hydroxyl groups. This is in contrast with the tin(II) chloride catalyzed reactions of diazomethane and diazophenylmethane in methanol with carbohydrates, glycerol and ribonucleosides, where the primary hydroxyl group does not react.

相关化合物

  • 顺式-1,2-环己二醇
  • 反式-1,2-环己二醇

相关文献：

Effect of ethanol on the urinary excretion of cyclohexanol and cyclohexanediols, biomarkers of the exposure to cyclohexanone, cyclohexane and cyclohexanol in humans.

1999-06-01

[Scand. J. Work. Environ. Health 25(3) , 233-7, (1999)]

Biological monitoring of occupational exposure to cyclohexane by urinary 1,2- and 1,4-cyclohexanediol determination.

1999-03-01

[Int. Arch. Occup. Environ. Health 72(2) , 115-20, (1999)]

Expression of benzene dioxygenase from Pseudomonas putida ML2 in cis-1,2-cyclohexanediol-degrading pseudomonads.

2001-06-01

[Appl. Microbiol. Biotechnol. 55(6) , 721-6, (2001)]

Insight into acid-mediated asymmetric spirocyclization in the presence of a chiral diol.

2000-10-01

[Chem. Pharm. Bull. 48(10) , 1536-40, (2000)]

Oxidation of cyclohexanediol derivatives with 12-tungstophosphoric acid-hydrogen peroxide system.

2009-01-01

[J. Oleo Sci. 58(6) , 323-8, (2009)]

更多文献...