102697-40-5

Basic information

• Product Name: 1-(4-Methanesulfonyl-phenyl)-2,2-dimethyl-3-methylene-cyclopropanecarboxylic acid ethyl ester
• Synonyms: 1-(4-Methanesulfonyl-phenyl)-2,2-dimethyl-3-methylene-cyclopropanecarboxylic acid ethyl ester
• CAS NO: 102697-40-5
• Molecular Weight: 308.398
• Mol File: 102697-40-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(4-Methanesulfonyl-phenyl)-2,2-dimethyl-3-methylene-cyclopropanecarboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Methanesulfonyl-phenyl)-2,2-dimethyl-3-methylene-cyclopropanecarboxylic acid ethyl ester(102697-40-5)
• EPA Substance Registry System: 1-(4-Methanesulfonyl-phenyl)-2,2-dimethyl-3-methylene-cyclopropanecarboxylic acid ethyl ester(102697-40-5)

Safety Data

• Hazardous Substances Data: 102697-40-5(Hazardous Substances Data)

Upstream product

• 18620-04-7 4-thioanisolemagnesium bromide 
• 62936-31-6 (4-methylsulfanylphenyl)oxoacetic acid ethyl ester 
• 598-25-4 Dimethylallene 
• 102697-44-9 (4-Methanesulfinyl-phenyl)-oxo-acetic acid ethyl ester 

Relevant articles and documents

Captodative Rate Enhancements in the Methylenecyclopropane Rearrangement

A series of 2-aryl-2-carbethoxy-3,3-dimethylmethylenecyclopropanes, 7, with substitution in the para position of the aromatic ring, have been prepared.These substrates rearrange thermally to 2-aryl-2-carbethoxyisopropylidenecyclopropanes, 8, by fragmentation of the cyclopropane bond which gives a biradical intermediate.Rates of this rearrangement are substituent-dependent.Electron-donor substituents such as p-OCH3 and p-SCH3 enhance the rearrangement rate to a greater extent than that predicted by their rate-enhancing effect on the "parent" system, 3-aryl-2,2-dimethylmethylenecyclopropane (4).This enhanced rearrangement rate is attributed to the captodative effect in which the acceptor carbethoxy group and the donor group on the aromatic ring exert a synergistic stabilizing effect on the benzylic portion of the biradical intermediate. p-Fluoro and p-methyl substituents are also capable of acting as true donor groups in captodative systems.Rearrangement rates of 7 containing electron-donor groups correlate with ?+ values, which are a measure of the donor abilities of various groups.The captodative effect has been used as a probe for the mechanism of stabilization of free radicals by the sulfinyl group, SOCH3.No captodative rate enhancement is observed when 7-p-SOCH3 is rearranged.This implies that stabilization of free radicals by the sulfinyl group does not involve utilization of the sulfur nonbonding electron pair in a donor fashion, but probably involves this group acting as an acceptor group.