Methylcyclohexyl ether

Another example is the hydrogenation of the homoallylic eompound 4-methyl-3-cyclohexenyl ethyl ether to a mixture of 4-methylcyclohexyl ethyl ether and methylcyclohexane. The extent of hydrogenolysis depends on both the isomerizing and the hydrogenolyzing tendencies of the catalysts. With unsupported metals in ethanol, the percent hydrogenolysis decreased in the order palladium (62.6%), rhodium (23 6%), platinum (7.1%), iridium (3.9%), ruthenium (3.0%) (S3). 

Anselmi et al. (02JCS(P2)1525), very recently published the conformational analysis and dynamics of cA/ rafts-4-methylcyclohexyl tetrahydro-pyranyl ethers (cf. Scheme 12) and compared their structures with the floral odors of the compounds. The cis isomer 40(cis), endowed with a main white flower note, has an bent, oval molecular shape. The trans derivatives 40(trans) and 41, exhibit different odors, possess an extended structure of cylindrical molecular shape. Brenna et al. (02CJC714) reexamined the configuration/conformation of rose oxide analogues. However, the conformational analysis provided poorer results than published previously (78JPC303) without even citing the previous paper. 

HYDROBORATION Bis(3,6-dimethyl)bore-pane. Bis(trans-2-methylcyclohexyl)bo-rane. Catecholborane. Dicyclohexylbo-rane. Diisopinocamphenylborane. 2,3-Dimethyl-2-butylborane. Dimethyl sul-fide-Borane. Monochloroborane-Diethyl etherate. 

The reaction of bicyclo[4.1.0]heptane with diborane and subsequent treatment with hydrogen peroxide produced predominantly cyclohexylmethanol (5b) in high yield.Under modified experimental conditions small amounts of isomeric methylcyclohexanol (6b) and cycloheptanol (7b) were isolated. In contrast to the hydroboration of alkenes, the cyclopropane cleavage reaction is inhibited by ethereal solvents such as diethyl ether, tetrahydrofuran or 2-methoxy-ethyl ether. Bicyclo[3.1.0]hexane reacted with diborane in a similar fashion to give mainly cyclopentylmethanol (5a).The reaction of l-methylbicyclo[4.1.0]heptane gave a mixture of cis- and tram-(2-methylcyclohexyl)methanol (5c) in an initial ratio of 60 40. Spiro[2.5]octane reacted with diborane to yield only products derived from scission at the spiro carbon. The main product was 2-cyclohexylethanol (8). ... 

Chloroethyl)-3-(4-methylcyclohexyl)-l-nitrosourea Chloromethyl methyl ether... 

An ethereal soln. of triphenylmethylsodium added rapidly with stirring to a soln. of 1-methylcyclohexanol in ether until a persistent red coloration indicates a slight excess of the base, phthalic anhydride added in one portion, stirring continued 1-2 hrs., then water added 1-methylcyclohexyl hydrogen phthalate. Y 85%. F. e. s. K. G. Rutherford, J. M. Prokipcak, and D. P. G. Fung, J. Org. Chem. 28, 582 (1963). 

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