77301-62-3

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 1504-55-8 (E)-3-phenyl-2-methyl-2-propenol 
• 7042-33-3 ethyl 2-methylcinnamate 

Downstream Products

• 77301-64-5 2,2-Dichlor-1-methyl-3c-phenyl-1r-cyclopropanmethanol-tetrahydro-2-pyranylether 
• 77301-64-5 2,2-Dichlor-1-methyl-3t-phenyl-1r-cyclopropanmethanol-tetrahydro-2-pyranylether 
• 176956-41-5 3-Bromo-5-(4-methoxy-phenyl)-4-methyl-2-phenyl-furan 

Relevant academic research and scientific papers

Highly stereoselective radical carbonylations of gem-dihalocyclopropane derivatives with CO

A couple of radical carbonylations of gem-dihalocyclopropanes 1 using CO and Bu3SnH (formylation) or Bu3Sn(CH2CH=CH 2) (allylacylation) successfully proceeded to give trans and cis adducts (2 and 3) with good to

Synthesis of 2,5-diaryl-3-halofurans via regioselective ring cleavage of aryl 3-aryl-2,2-dihalocyclopropyl ketones

Several aryl 3-aryl-2,2-dihalocyclopropyl ketones were converted to 2,5-diaryl-3-halofurans in the presence of aluminum chloride via regioselective gem-dihalocyclopropane ring-cleavage. Friedel-Crafts acylation of substituted benzenes with 3-aryl-2,2-dihalocyclopropanecarbonyl chlorides followed by this furan formation also proceeded in a one-pot manner. For functionalization, bromine on a furan ring was easily replaced by methyl and carboxyl groups; lithiation using butyllithium followed by the treatment with iodomethane and carbon dioxide, respectively.

Synthesis and stereostructure-activity relationship of a synthetic pyrethroid, 2-chloro-1-methyl-3-phenylcyclopropylmethyl 3-phenoxybenzyl ether

Of the four diastereoisomers of 2-chloro-1-methyl-3-phenylcyclopropylmethyl 3-phenoxybenzyl ether 5, a new type of synthetic pyrethroid, which have been synthesized, only the (1R*,2S*,3S*)-isomer 5a showed significant insecticidal activity against the tobacco cutworm and the common mosquito. Two enantiomers (1R,2S,3S)-(-)-5a and (1S,2R,3R)-(+)-5a were prepared by the optical resolution process, and their absolute configurations were determined by chemical derivatization via predictable asymmetric cyclopropanation. Bioassay showed that the (1R,2S,3S)-(-)-5a was active, while (1S,2R,3R)-(+)-5a was not. The geometry around the asymmetric centre of the (1R,2S,3S)-enantiomer was correlated with that of representative pyrethroids which are both optically active and have insecticidal activity.

Novel Synthetic Pyrethroid Containing a Halocyclopropane Structure

A new class of synthetic pyrethroid, 2-halo-3-arylcyclopropyl-methyl 3-phenoxybenzyl ethers (1a-h), exhibited significant insecticidal activity against tobacco cutworm and housefly.

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.