18508-90-2

Upstream product

• 21862-63-5 trans-4-tert-butylcyclohexanol 
• 124-63-0 methanesulfonyl chloride 
• 98-53-3 4-tercbutyl-cyclohexanone 

Downstream Products

• 75809-00-6 cis-1-phenylselenenyl-4-tert-butylcyclohexane 
• 10411-92-4 cis-4-tert-butylcyclohexyl acetate 
• 123185-94-4 cis-4-tert-butyl-1-(tert-butylthio)cyclohexane 
• 22803-98-1 Ethyl cis-(4-tert-butylcyclohexyl)-2-cyanoacetate 
• 59277-55-3 cis-1-tert-butyl-4-phenylsulfanyl-cyclohexane 
• 15867-50-2 cis-4-t-butylcyclohexyl benzoate 
• 123185-95-5 cis-4-tert-butyl-1-(tert-butylsulfinyl)cyclohexane 
• 1225352-09-9 2-bromo-6-(trans-4-tert-butylcyclohexyloxy)naphthalene 
• 1393450-80-0 6-bromo-2-(4-tert-butylcyclohexyloxy)quinazoline 
• 1393449-29-0 ethyl 1-((6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methyl)-4-methylpiperidine-4-carboxylate 
• 1266115-60-9 6-(trans-4-tert-butylcyclohexyloxy)-2-naphthaldehyde 
• 1393449-55-2 ethyl 1-((6-((trans-4-(tert-butyl)cyclohexyl)oxy)naphthalen-2-yl)methyl)-3-methylpiperidine-4-carboxylate 
• 1225352-13-5 6-bromo-2-(trans-4-tert-butylcyclohexyloxy)-1-iodonaphthalene 
• 1266119-64-5 1-(6-((trans-4-(tert-butyl)cyclohexyl)oxy)naphthalen-2-yl)ethanone 

Relevant academic research and scientific papers

Cyclopropenone catalyzed substitution of alcohols with mesylate ion

The cyclopropenone catalyzed nucleophilic substitution of alcohols by methanesulfonate ion with inversion of configuration is described. This work provides an alternative to the Mitsunobu reaction that avoids the use of azodicarboxylates and generation of hydrazine and phosphine oxide byproducts. This transformation is shown to be compatible with a range of functionality. A cyclopropenone scavenge strategy is demonstrated to aid purification.

The Use of Precise Structural Information for the Understanding of the Conformational Behavior of cis-5-(tert-Butylsulfonyl)- and cis-5(tert-Butylsulfinyl)-2-tert-butyl-1,3-dioxane

A single-crystal X-ray structure determination of the title sulfoxide (cis-2) was carried out and compared with data previously reported for the corresponding sulfone (cis-1).Whereas the latter adopts an eclipsed conformation (one S-C/C-H and two S=O/C-C eclipsed bond pairs), both the tert-butyl and the S=O group in the sulfinyl function point outside the ring in a staggered rotamer.A substantial difference in length for the endocyclic C-C bonds in cis-2 suggests the effect of through-space ?C-C/?*S-O (attractive) and ?C-C/nS (repulsive) interactions and/or ?C-H -> ?*C-S stereoelectronic mechanisms.The X-ray diffraction study of the cyclohexane analogue (cis-4) shows again a staggered conformation for the tert-butylsulfinyl group, but confirms the repulsive steric hindrance between the gauche t-BuS and endocyclic methylene groups.The contrasting behavior between the sulfone and sulfoxide groups points to the existence of an attractive interaction S=O/C-C, which stabilizes the eclipsed conformer in cis-1 and overcomes the torsional strain in the eclipsed bond pair S-C/C-H.The nature of the stabilizing S=O/C-C interaction is proposed in the light of recent theoretical calculations.

A PROCEDURE FOR ALCOHOL INVERSION USING CESIUM ACETATE

A convenient and efficient procedure for alcohol inversion by means of the reaction of mesylates or alkyl halides with cesium acetate is described.