38858-74-1Relevant articles and documents
Efficient Simmons-Smith cyclopropanation with Zn/Cu and CH 2I2
Fujii, Kanami,Shiine, Kodai,Misaki, Tomonori,Sugimura, Takashi
, p. 69 - 72 (2013)
An appropriate solvent to perform the original Simmons-Smith reaction was reinvestigated. Among available solvents, cyclopentyl methyl ether (CPME), a recently commercialized ethereal solvent, was found to be the best so far. Compared with Et2O under reflux - the commonest conditions - reaction completion in CPME at 50 °C was about 10 times faster. The product yields and selectivities were mostly identical to those with Et2O, but were better in some cases; e.g. 13-56% with 2-cyclohexenol. The good performance of CPME should be mainly due to its moderate polarity and high boiling point. Copyright
Reaction of Enol Ethers with Zinc Carbenoid Reagents. Cyclopropanation and Subsequent Isomerization to Allylic Ethers
Ryu, Ilhyong,Aya, Tomoyuki,Otani, Shoji,Murai, Shinji,Sonoda, Noboru
, p. 279 - 290 (2007/10/02)
The reactions of enol ethers (ROC=C, R= alkyl, silyl) with zinc carbenoid reagents were found to give allylic ethers in several cases along with the expected cyclopropyl etehrs.The ratio of these two products was highly dependent on the concentration of t
