73611-76-4

Upstream product

• 7500-91-6 methyl 2-methyl-1-oxocyclohexane-2-carboxylate 
• 930-68-7 cyclohexenone 
• 17640-15-2 methyl cyanoformate 
• 74-88-4 methyl iodide 
• 73611-71-9 2-Methyl-7-oxa-bicyclo[4.1.0]heptane-2-carboxylic acid methyl ester 
• 41302-34-5 2-(methoxycarbonyl)cyclohexanone 
• 343786-98-1 Methyl 2-Hydroxy-1-methyl-3-cyclohexenoate 

Downstream Products

• 116868-95-2 (+/-)-methyl 1,3-dimethyl-2-oxo-3-cyclohexene-1-carboxylate 

Relevant academic research and scientific papers

Synthesis of Novel Pyrazolobenzisoxazole Ring Systems via a 1,3-Dipolar Cycloaddition Reaction

Compounds containing the novel 2H-pyrazolobenzisoxazole 2 and 4H-pyrazolo-1,2-benzisoxazole 3 ring systems have been synthesized via a 1,3-dipolar cycloaddition reaction between acetonitrile oxide and the tetrahydroindazole 1.

Some 6,6-disubstituted 2,4-cyclohexadien-1-ones and the facial selectivity in their Diels-Alder reactions with dimethyl acetylenedicarboxylate

6,6-Disubstituted 2,4-cyclohexadien-1-ones can be prepared by dibromination-bisdehydrobromination of the corresponding 6,6-disubstituted 2,2-dibromocyclohexanones.Such dienes undergo Diels-Alder reactions with dimethyl acetylenedicarboxylate to give 3,3-disubstituted 5,6-di(methoxycarbonyl)bicycloocta-5,7-dien-2-ones; when the substituents at C-6 in the dienones are different, two diastereomers of the adducts are formed in a ratio dependent on the "facial selectivity" in the Diels-Alder reactions.For the cases where one of the 6-substituents is methyl and the other is methoxycarbonyl, acetoxymethyl, dibromomethyl, or dichloromethyl it has been established via X-ray crystallograpfy and chemical correlation that the endo-3-methyl/exo-3-methyl product ratio is 3.0, 0.9, 8, and 6, respectively.The origin of these differences is discussed briefly and a spectroscopic method for the assignment of structures to the individual diastereomers is proposed.Key words: Diels-Alder reactions, substituted 2,4-cyclohexadien-1-ones, facial selectivity, dimethyl acetylenedicarboxylate.

Preparation of Allylic Alcohols from Epoxides Using Iodotrimethylsilane

The transformation of epoxides into allylic alcohols by use of iodotrimethylsilane and 1,5-diazabicycloundec-5-ene is described.The scope and limitations of this reaction are examined.This method is complementary to the method of Sharpless in the case of trisubstituted epoxides and proceeds under milder reaction conditions than the method employing lithium dialkylamides.