91405-18-4

Upstream product

• 63089-64-5 2-(4-tert-butyl-1-cyclohexenyl)-2-methylpropiononitrile 
• 91405-12-8 2-(cis-4-(tert-butyl)-cyclohexyl)-2-methylpropionitrile 
• 91405-11-7 2-(trans-4-(tert-butyl)-cyclohexyl)-2-methylpropionitrile 
• 93937-74-7 4β-(tert-butyl)-β-(1-methylvinyl)-1α-cyclohexanecarboxaldehyde 
• 91405-15-1 4β-(tert-butyl)-1α-(1-methylvinyl)cyclohexanecarbaldehyde 

Relevant academic research and scientific papers

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.

Protolytic Opening of Two Diastereoisomeric Cyclopropanols

Cob(I)alamin (1(I))-catalyzed reduction of the aldehyde 2 led to the two crystalline cyclopropanols 3 and 4 (see Scheme 2).The protolytic ring-opening starting from 3 produced the saturated aldehydes 6 and 7; 8 was formed in traces only (see Scheme 3).The

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.