Cyclohexyl methyl

Electrostatic potential map for methyl cyclohexyl sulfoxide shows negatively-charged regions (in red) and positively-charged regions (in blue), either of which is capable of sticking to a polar stationary phase. 

Methylsulfinyl cyclohexyl ketone gives >95 % yield of methyl cyclohexyl ketone as a colorless liquid, mp of semicarbazone 172-174°. 

Radical cyclization. Ring closure of hept-6-en-1 -y 1 radical yields two products, methyl-cyclohexyl radical (85 percent) and cycloheptyl radical (15 percent).39 The overall rate constant is 3.5 X 104 s l. What are the rate constants for each pathway ... 

Benzenesulfomc aad, 4-methyl-, cyclohexyl ester [Cyclohexanol, p-toluenesul-fonate], 55, 112... 

CN rranj -2-[[[4-[[(aminoiminomethyl)amino]methyl]cyclohexyl]carbonyl]oxy]benzoic acid phenylmethyl ester... 

CN [liP,16p,21(tranj)]-21-[[[4-[(acetylamino)methyl]cyclohexyl]carbonyl]oxy]-9-chloro-l 1,17-dihydroxy-16-methylpregna-1,4-dicne-3,20-dione... 

Ketones such as methyl cyclohexyl ketone 1284 react with DMSO/TCS 14, via their enol form, to give 21% of the chloroketone 1285 a and 63% of the a-methyl mercaptoketone 1286 [70]. Reaction of 1284 with DMSO/MesSiBr (TBS) 16 affords 85% of the bromo compound 1285 b and 12% hexahydrophenacyl bromide 1287 but no 1286 [71]. Whereas reaction of tra s-4-phenyl-3-buten-2-one (benzalacetone) 1288 with DMSO/TCS 14 gives 81% of the sulfonium salt 1289 [70], the y9-dicar-bonyl compound ethyl acetoacetate furnishes 69% of 1290 [70]. In contrast with DMSO/TCS 14, the combination DMSO/TBS 16 effects selective monobromina-tion of y9-dicarbonyl compounds [71] (Scheme 8.28). 

We have shown that a number of aliphatic ethers, containing steric-ally accessible p-hydrogen atoms, are cleaved in good yield when the tetrahalogenoanthranilic acids are diazotised in ethers 128,59). Diethyl ether is cleaved to the tetrahalogenophenetole (90) and methyl-cyclohexyl ether affords the tetrahalogenoanisole. In this latter reaction we were able to detect cyclohexene and therefore a plausible, but as yet unproved, mechanism is as shown. 

Early studies of the asymmetric reduction of prochiral ketones by chiral aluminum alkoxides have been reviewed by Morrison and Mosher (1). Doering and Young (123) reported the reduction of methyl cyclohexyl ketone with chiral 3-methyl-2-butanol in the presence of a catalytic amount of aluminum alkoxide to give the (S)-( + )-carbinol in a 22% optical yield. Jackman and co-workers (124) similarly reduced methyl n-hexyl ketone with chiral 3,3-dimethyl-2-butanol to the (S)-( - )-carbinol in a 6% optical yield. Other attempts resulted in similar low optical yields or gave only racemic products. Since the reductions were carried out under equilibrium conditions, racemization could have accounted for the low optical yields. 

Complex hydrides were used for reductions of organometallic compounds with good results. Trimethyllead chloride was reduced with lithium aluminum hydride in dimethyl ether at —78° to trimethylplumbane in 95% yield [1174, and 2-methoxycyclohexylmercury chloride with sodium borohydride in 0.5 n sodium hydroxide to methyl cyclohexyl ether in 86% yield [1175]. 

Bis-[[decafluoro-3-(difluoro-hydroxy-methyl)-cyclohexyl]-difluoro-mclhyl]- -(difluoro-hyd roxy-methyl)-nonafluoro-ElOa, 190 (H -> F Arenc + F2)... 

Base-promoted E2 elimination involves simultaneous loss of H+ and X from neighboring carbons. Applying this rule to 2-methyl cyclohexyl tosylate suggests that two different products might form, but the actual situation is more complicated. One tosylate isomer gives only one of the two possible alkenes, while the other gives both. 

Sipalin AOM. Ger trade name for the methyl-cyclohexyl ester of adipic acid. It was incorporated in solvents for NC (such as 75/25 butyl acetate/ethyl ale), the soln being used to coat electric detonator fuseheads by a dipping procedure. The Sipalin resulted in a NC varnish coating which was less permeable to moisture and less readily cracked... 

Answer VII-c is an unsymmetrical aliphatic etlicr (I -methyl cyclohexyl ethyl ether). 

Answer XlV-f is an a./3-unsaturated ketone [ Hl-methyl-cyclohexyl)-I-penten-3-oneJ. 

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