543724-50-1

Upstream product

• 4746-97-8 cyclohexanedione monoethylene ketal 
• 952589-06-9 (1R,4R)-4-((tert-butyldiphenylsilyl)oxy)cyclohexanol 
• 543724-48-7 tert-butyl-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-diphenyl-silane 
• 22428-87-1 4,4-ethylenedioxycyclohexan-1-ol 
• 130745-59-4 4-<(tert-Butyldiphenylsilyl)oxy>cyclohexanone 

Downstream Products

• 543724-55-6 3-(tert-butyl-diphenyl-silanyloxy)-6-hept-6-enylidene-cyclohex-1-enecarbaldehyde 
• 543724-54-5 (3-bromo-4-hept-6-enylidene-cyclohex-2-enyloxy)-tert-butyl-diphenyl-silane 
• 543724-51-2 2-bromo-4-(tert-butyl-diphenyl-silanyloxy)-cyclohex-2-enone 

Relevant academic research and scientific papers

METHOD FOR PRODUCING CARBONYL COMPOUND AN PRO-OXIDANT USED FOR PRODUCTION OF CARBONYL COMPOUND

The invention provides a process for the preparation of a carbonyl compound in high efficiency by oxidizing an alcohol. The process for the preparation of a carbonyl compound of the present invention includes a step of oxidizing an alcohol in the presence of a compound of the formula (I) or a derivative or a salt thereof, and an oxidant, wherein R1 and R2 independently represent hydrogen, a halogen, a nitro or acidic group, or an alkyl or alkoxy group, each of which optionally has a substituent, or R1 and R2 combine the two carbon atoms to which they are boned to form an aromatic ring.

2-iodoxybenzenesulfonic acid as an extremely active catalyst for the selective oxidation of alcohols to aldehydes, ketones, carboxylic acids, and enones with oxone

Electron-donating group-substituted 2-iodoxybenzoic acids (IBXs) such as5-Me-IBX (1g), 5-MeO-IBX (1h), and 4,5-Me2-IBX were superior to IBX 1a as catalysts for the oxidation of alcohols with Oxone (a trad emark of DuPont) under nonaqueous conditions, although Oxone was almost insoluble in most organic solvents. The catalytic oxidation proceeded more rapidly and cleanly in nitromethane. Furthermore, 2-iodoxybenzenesulfonic acid (IBS, 6a) was much more active than modified IBXs. Thus, we established a highly efficient and selective method for the oxidation of primary and secondary alcohols to carbonyl compounds such as aldehydes, carboxylic acids, and ketones with Oxone in nonaqueous nitromethane, acetonitrile, or ethyl acetate in the presence of 0.05-5molpercentof 6a, which was generated in situ from 2-iodobenzenesulfonic acid (7a) or its sodium salt. Cycloalkanones could be further oxidized to α,β- cycloalkenones or lactones by controlling the amounts of Oxone under the same conditions as above. When Oxone was used under nonaqueous conditions, Oxone wastes could be removed by simple filtration. Based on theoretical calculations, we considered that the relatively ionic character of the intramolecular hypervalent iodine-OSO2 bond of IBS might lower the twisting barrier of the alkoxyperiodinane intermediate 16.

A diene-transmissive approach to the quassinoid skeleton

Several tetracyclic molecules were prepared by diene-transmissive Diels-Alder cycloadditions. Control over the stereochemical outcome of the cycloaddition was achieved and the structural features of the precursors affecting the stereochemistry is discussed. Useful information was gathered concerning the factors governing this stereocontrol, which will be indispensable for the future of this strategy.