78796-69-7

Upstream product

• 1165952-91-9 cyclohexa-1,3-diene 
• 2570-63-0 thallium(III) triacetate 
• 64-19-7 acetic acid 
• 546-67-8 lead(IV) tetraacetate 
• 110-83-8 cyclohexene 
• 108-24-7 acetic anhydride 
• 76644-52-5 rac-3-acetoxycyclohexene 

Downstream Products

• 91210-43-4 C₂₂H₄₂O₄Si₂ 
• 91210-42-3 (3S,4R)-3,4-Bis-[1-(tert-butyl-dimethyl-silanyloxy)-vinyloxy]-cyclohexene 
• 28981-66-0 (+/-)-3,4-dideoxyconduritol D 

Relevant academic research and scientific papers

Hydroxyhalogenations of acyloxycyclohex-2-enes. Part 3. Iterative 1,2-hydroxyiodination of acetoxycyclohex-2-ene: Preparation of tetraacetyl conduritol D

Compound 22, the tetraacetyl derivative of conduritol D, has been synthesized by repeated hydroxyiodination reactions in nine steps from acetoxycyclohex-2-ene.

REACTION OF 1,3-CYCLOHEXADIENE WITH THE ACETIC ACID-ACETIC ANHYDRIDE SYSTEM INITIATED BY MANGANESE(III) ACETATE

The reaction of 1,3-cyclohexadiene with the acetic acid-acetic anhydride system in the presence of manganese(III) acetate was studied.The reaction products were a mixture of the stereoisomers of 2-acetoxy-3-cyclohexenyl- and 4-acetoxy-2-cyclohexenylacetic acid and also 3,4- and 3,6-diacetoxy-1-cyclohexene.The mixture of acetoxy acids was converted into the corresponding hydroxy acids, and the diacetoxycyclohexenes were converted into the corresponding saturated esters.The cis-lactone was obtained as the only reaction product from the mixture of stereoisomersof the γ- and ε-hydroxy acids, while the methyl esters were obtained from the ε-hydroxy acids.

Diastereospecific Hydroxyiodination of 1-Acetoxycyclohex-2-ene via Intramolecular Delivery of Oxygen

The previously unreported reaction of N-iodosuccinimide with acetoxycyclohex-2-ene to give monoacetates of 3-iodocyclohexane-1,2-diols is diastereospecific.

Catalytic One-Pot Osmylation of Cyclohexadienes: Stereochemical and Conformational Studies of the Resulting Polyols

Catalytic double osmylation is described for a series of cyclohexadienes in acetone/H2O in the presence of the co-oxidant N-methylmorpholine N-oxide (NMO).The formation of polyols occurred stereospecifically with cyclohexadienes 3, 7, and 11a, leading thereby to tetrols 5a, and 9a and to allo-inositol (14a), respectively.To the contrary, trans-cyclohexadiene-diol 15a gave a mixture of the stereoisomeric inositols 18a (epi), 19a (neo), and 20a (chiro).High-field NMR let to clearcut conformational analyses of the polyhydroxylated derivatives.

DIACETOXYLATION OF CONJUGATED DIENES WITH THALLIUM(III) ACETATE IN ACETIC ACID

The reaction of conjugated dienes such as 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, 2,5-dimethyl-2,4-hexadiene, 1,3-cyclopentadiene, and 1,3-cyclohexadiene with thallium(III) acetate in acetic acid at 10-65 deg C for 0.5-15 hr affords an isomeric mixture of the corresponding diacetoxyalkenes (1,2- and 1,4-addition products) in 10-92 percent yields.The 1,2-addition products are predominantly formed in all cases examined except the case of 1,3-cyclopentadiene.The reaction is assumed to proceed through acetoxythallation and dethallation steps, the latter step being accompanied and/or followed by an attack of acetoxyl group.An initial attack of thallium moiety is proposed to occur mainly at C-1 and C-2 carbons in the cases of linear terminal dienes and cyclic dienes, respectively.