60041-30-7Relevant academic research and scientific papers
Evaluation of Chelation Effects Operative during Diastereoselective Addition of the Allylindium Reagent to 2- And 3-Hydroxycyclohexanones in Aqueous, Organic, and Mixed Solvent Systems
Paquette, Leo A.,Lobben, Paul C.
, p. 5604 - 5616 (2007/10/03)
The unprotected 2- and 3-hydroxycyclohexanones 1-8 were prepared by methods that skirted as much as possible their proclivity for α-ketol rearrangement (where the possibility for such isomerization exists). The diastereofacial selectivity of their reactio
Reactions of 1-Methyl-4-t-butylcyclohexene and 1-Methylcyclohexene with Thallium(I) Acetate-Iodine
Cambie, Richard C.,Hume, Bruce A.,Rutledge, Peter S.,Woodgate, Paul D.
, p. 413 - 419 (2007/10/02)
Treatment of 1-methyl-4-t-butylcyclohexene (2) with thallium(I)acetate-iodine in wet acetic acid at 90 deg C gives a complex mixture of products, which differs from that obtained from a Woodward reaction with silver(I) acetate followed by hydrolysis and which includes the unexpected hydroxy-iodoacetate (25).At 20 deg C the thallium(I)-mediated reaction gives a mixture of regioisomeric iodo-acetates.A re-investigation of the reaction of thallium(I) acetate-iodine with 1-methylcyclohexene (1) at 20 deg C has shown that this is not highly regioselective as reported earlier.The actions of KOAc-I2-18-crown-6 and iodine(III) triacetate in acetic acid on the alkenes (1) and (2), and of I2-H2O in tetramethylene sulphone-chloroform on the alkene (2) are reported.
Stereoselective Synthesis of Alcohols, I Synthesis of One-Carbon Homologous Allyl Alcohols from Aldehydes or Ketones
Hoffmann, Reinhard W.,Goldmann, Siegfried,Maak, Norbert,Gerlach, Rainer,Frickel, Fritz,Steinbach, Gertrud
, p. 819 - 830 (2007/10/02)
The high yield conversion of aldehydes and ketones 2 to the one-carbon homologous allyl alcohols 3 is achieved by condensation to the vinyl sulfoxides 7, isomerisation to the allyl sulfoxides 9, and subsequent sigmatropic rearrangement.
Stereoselective Synthesis of Alcohols, IV Conformational Factors Determining the Stereochemistry of the Allyl Sulfoxide/ Allyl Sulfenate-Rearrangement
Hoffmann, Reinhard W.,Gerlach, Rainer,Goldmann, Siegfried
, p. 856 - 863 (2007/10/02)
The stereochemistry of the sigmatropic rearrangement of the conformationally rigid allyl sulfoxides 5 revealed a 6.2 fold preference for axial formation of the new C-O-bond.This preference dominates the 3.1 fold preference for an exo-versus endo-tran
