91405-17-3

Upstream product

• 63089-64-5 2-(4-tert-butyl-1-cyclohexenyl)-2-methylpropiononitrile 
• 91405-15-1 4β-(tert-butyl)-1α-(1-methylvinyl)cyclohexanecarbaldehyde 
• 93937-74-7 4β-(tert-butyl)-β-(1-methylvinyl)-1α-cyclohexanecarboxaldehyde 
• 64-19-7 acetic acid 

Downstream Products

• 91405-04-8 2-(4-(tert-butyl)-1-cyclohexeny)-2-methylpropanol 
• 91405-14-0 2-(cis-4-(tert-butyl)cyclohexyl)-2-methylpropanol 
• 41342-83-0 2-(4-tert-Butyl-phenyl)-2-methyl-propan-1-ol 

Relevant academic research and scientific papers

219. Cob(I)alamin-Catalyzed Skeletal Migrations Observed during the Reduction of 4β-(tert-Butyl)-1α-(1-methylvinyl)cyclohexanecarbaldehyde

The cob(I)alamin(1(I))-catalyzed transformation of the aldehyde 2 has been studied (cf.Table 1).Kinetic examinations showed a rapid isomerization of 2 to 3 (cf.Fig. 1 and 2).From the transformations in glacial AcOH, the two cyclopropanols 5 and 7 were iso

Skeletal Migrations Observed during the Cob(I)alamin-Catalyzed Reduction of 4β-(tert-Butyl)-1β-(1-methylvinyl)cyclohexanecarbaldehyde

During the cob(I)alamin(1(I))-catalyzed reduction of 3, intermediate formation of 2 and final generation of 4-10 was observed (see Scheme 1, cf.Tables 1 and 2).Identical products in similar ratios were generated starting from either 2 or 3.Accepting the intermediate formation of six interconnected cobalt complexes, i.e.A-F (cf.Sceme 2), the generation of all the products observed can be explained.

Oxidative Cyclopropanol Opening by Cob(III)alamin

Starting from the cyclopropanol 2, the isomeric cyclopropanol 4 and th β,γ-unsaturated aldehydes 7 and 8 have been produced by a cobalamin-dependant transformation.In traces, the two acetoxycyclopropanes 3 and 6, the saturated aldehydes 5 and 11 and the β,γ-unsaturated aldehyde 9 could be detected (cf.Structural Formulae and Table).Starting from 4 the same products in a rather similar distribution were obtained.The isomerization 24 as well as the transformations leading to 7, 8, and 9 are shown to be mediated by cob(III)alamin (1(III)).The results are explained on the basis of rearranging Co-complexes.The migrations might driven by the elctrophilic nature of the central Co(d6)-atom.

Cob(I)alamin Differentiating Alkenes During Saturation

The olefins 2, 7, 11, and 19 have been reduced using catalytic amounts of cob(I)alamin(1(I)).During a slow saturation, the catalyst is able to differentiate the two diastereotopic faces of the endocyclic double bonds in 11 (t1/2 40 d) and 19 (t1/2 80 d, cf.Scheme 4).The substrates 2 (t1/2 1 h, cf.Scheme 2) and 7 (t1/2 4 h, cf.Scheme 3) are reduced much faster.A rationalization of the data can be obtained formulating tertiary alkylcobalamins as intermediates.Of the oxime 6 ( cf.Scheme 2) and the p-bromobenzoate 23 (cf.Scheme 5) the structures have been determined by X-ray analysis.