65354-73-6

Basic information

• Product Name: Cyclopropanecarboxylic acid, 2-(1-methylethylidene)-1-phenyl-, ethyl ester
• CAS NO: 65354-73-6
• Molecular Formula: C15H18O2
• Molecular Weight: 230.307
• Mol File: 65354-73-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Cyclopropanecarboxylic acid, 2-(1-methylethylidene)-1-phenyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarboxylic acid, 2-(1-methylethylidene)-1-phenyl-, ethyl ester(65354-73-6)
• EPA Substance Registry System: Cyclopropanecarboxylic acid, 2-(1-methylethylidene)-1-phenyl-, ethyl ester(65354-73-6)

Safety Data

• Hazardous Substances Data: 65354-73-6(Hazardous Substances Data)

Upstream product

• 22065-57-2 ethyl 2-phenyldiazoacetate 
• 598-25-4 Dimethylallene 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 849945-21-7 ethyl 2-phenyl-2-(2-tosylhydrazono)acetate 
• 65354-67-8 2,2-Dimethyl-3-methylene-1-phenyl-cyclopropanecarboxylic acid ethyl ester 

Relevant articles and documents

THE EFFECT OF THE TRIFLUOROMETHYL GROUP ON THE METHYLENECYCLOPROPANE REARRANGEMENT

The CF3 group, in conjunction with an electron donor group, can enhance the rate of the methylenecyclopropane rearrangement.This is attributed to captodative radical stabilization of the intermediate biradical.

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.

Regioselectivity in the Addition of Singlet and Triplet Carbenes to 1,1-Dimethylallene. A Probe for Carbene Multiplicity

Singlet carbenes add preferentially to the more substituted bond of 1,1-dimethylallene (1), to give methylenecyclopropanes 3 as the major product.In contrast, many triplet carbenes add with differing regioselectivity, giving the thermodynamically preferre