92173-10-9

Upstream product

• 7686-78-4 diethyl 2-vinylcyclopropane-1,1-dicarboxylate 

Downstream Products

• 136744-64-4 diethyl (E)-(1-benzyl-2-butenyl)malonate 
• 131061-77-3 (1R,4S,5S,6R)-4-Methyl-2-oxo-6-phenylethynyl-3-oxa-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester 
• 131061-77-3 (1R,4S,5S,6S)-4-Methyl-2-oxo-6-phenylethynyl-3-oxa-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester 
• 131061-73-9 (1S,4R,5R,6R)-6-Cyclohex-1-enyl-4-methyl-2-oxo-3-oxa-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester 
• 131061-73-9 (1S,4R,5R,6S)-6-Cyclohex-1-enyl-4-methyl-2-oxo-3-oxa-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester 
• 131061-75-1 (1S,4R,5R,6S)-4-Methyl-2-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester 
• 133-08-4 diethyl butylmalonate 
• 136744-63-3 diethyl (E)-(1-phenyl-2-butenyl)malonate 

Relevant academic research and scientific papers

BIS(TRIMETHYLSILYL) SULPHATE CATALYZED γ-LACTONIZATION OF CYCLOPROPANECARBOXYLATES HAVING A CARBONYL SUBSTITUENT AT CYCLOPROPANE α-CARBON

The oxa analogue of vinylcyclopropane rearrangement in the title system is carried out under mild conditions with the aid of the silicon Lewis acid catalyst.

Bis(trimethylsilyl) Sulfate Catalysis in γ-Lactonization of Cyclopropanecarboxylates Activated by Carbonyl Substituents on α-Carbon

The title reaction of 1-carbonyl substituted cyclopropanecarboxylates proceeds under C(1)-C(2) bond cleavage to produce γ-lactones.Stereochemically, the reaction takes two pathways: (1) substrates with a cationstabilizing group like vinyl on C(2) give thermodynamically favored γ-lactones having the thermodynamically more stable arrangement of substituents irrespective of the configuration of the cyclopropane substrates, (2) substrates without such a cation-stabilizing group afford γ-lactones under ca. 70percent inversion at C(2) reaction center.