34265-90-2

Upstream product

• 2650-40-0 3,3,5,5-tetramethyl cyclohexanol 
• 34265-89-9 3-methoxy-1,5-dimethyl-3-bora-bicyclo[3.3.1]non-6-ene 
• 127562-51-0 3,3,5,5-tetramethyl-1-piperidinocyclohexene 
• 32784-73-9 tris(2-methyl-2-propenyl)borane 
• 34242-17-6 1,5-dimethyl-3-(4-methyl-penta-1,4-dienyl)-3-bora-bicyclo[3.3.1]non-6-ene 
• 34265-88-8 1,5-dimethyl-3-(2-methyl-allyl)-3-bora-bicyclo[3.3.1]non-6-ene 

Downstream Products

• 24770-64-7 1,1,3,3-tetramethylcyclohexan 
• 32264-57-6 4,4,6,6-tetramethylcyclohex-2-en-1-one 

Relevant academic research and scientific papers

Dehydration of secondary alcohols via thermolysis of in situ generated alkyl diphenyl phosphates: An inexpensive and environmentally compatible method for the preparation of alkenes

Secondary alcohols are converted into diphenyl phosphate esters by the action of triphenyl phosphate or diphenyl phosphorochloridate in high-boiling, water-miscible solvents in the presence of base. The alkyl diphenyl phosphates undergo thermolysis to afford high yields of alkenes which distill from the reaction mixtures. Purification of the products is achieved by extraction with dilute sulfuric acid which removes traces of solvent and base that may have codistilled. The ratios of 2- (14) and 3-menthene (15), obtained from menthol (13) and neomenthol (16), and the formation of rearranged alkenes by 1,2-shifts from 3, 6, and 3,3-dimethylbutan-2-ol are consistent with ionic intermediates of the elimination reaction. The novel dehydration method offers distinct and important advantages over the existing methods.

Hydroboration. 86. Convenient Conversion of Aldehydes and Ketones into the Corresponding Alkenes via Hydroboration of their Enamines. A Remarkably Simple Synthesis of Either (Z)- or (E)-Alkenes

Aldehydes and ketones are converted into the corresponding alkenes via hydroboration of their enamines.Hydroboration of aldehyde enamines by 9-borabicyclononane (9-BBN), followed by methanolysis, affords the corresponding terminal alkenes in 75-90percent yields.Unsaturated aldehyde enamines produce the corresponding dienes under these conditions.Enamines derived from substituted cyclic ketones and heterocyclic ketones are readily accommodated in this reaction to afford the corresponding alkenes in very good yields.The synthesis of pure (Z)- or (E)-alkenes is readily achieved from the same acyclic ketone enamine by modification of the hydroboration-elimination procedure: (A) hydroboration by 9-BBN followed by methanolysis or (B) hydroboration by borane methyl sulfide (BMS) followed by methanolysis and hydrogen peroxide oxidation.Mechanistic rationale is provided.