77301-67-8

Upstream product

• 77301-64-5 2,2-Dichlor-1-methyl-t-3-phenyl-r-1-cyclopropanmethanol-tetrahydro-2-pyranylether 
• 94559-06-5 1-Chlor-c-2-methyl-c-3-phenyl-t-2-(tetrahydro-2-pyranyloxymethyl)-r-1-cyclopropancarbonsaeure-methylester 
• 124-38-9 carbon dioxide 

Downstream Products

• 100046-53-5 r-5-Hydroxy-2-methyl-3-phenyl-t-4-(2,2,6,6-tetramethyl-1-piperidyl)-2-cyclopenten-1-on 
• 100046-52-4 c-2-(Hydroxymethyl)-t-2-methyl-c-3-phenyl-1-(2,2,6,6-tetramethyl-1-piperidyl)-r-1-cyclopropancarbonsaeurelacton 
• 77301-71-4 1-tert-Butoxy-2t-methyl-3c-phenyl-1r,2c-cyclopropandimethanol 
• 77301-70-3 1-tert-Butoxy-2c-hydroxymethyl-2t-methyl-3c-phenyl-1r-cyclopropancarbonsaeure-lacton 

Relevant academic research and scientific papers

Reaction of 2,2-Dichloro-1-methyl-3-phenylcyclopropanemethanol Tetrahydropyranyl Ether with Butyllithium / CO2 and Subsequent Reactions of the Products

While the title reaction starting from 2a followed by acidic work-up affords only the α-chlorolactone 1 with low yield, alcaline work-up and addition of dimethyl sulfate lead to a mixture of the esters 2b and c and the chlorocyclopropene 3a.From 2b/c with

Mechanism of the Substitution at the Cyclopropane Ring

Starting from 2a the bicyclic chlorolactone 14a is obtained via 3a and 11a.Reaction of 14a with KOtBu gives the lactone 17b which also is formed from 14b.These results can be explained by a mechanism via the intermediate E.Additional evidence is given by the failure of 15a and b to react with KOtBu and by the product distribution of the reaction of deuterated compound 16a.