5108-87-2Relevant academic research and scientific papers
Microwave-promoted synthesis of β-hydroxyesters by the Reformatsky reaction in the absence of solvent
Gholap, Atul R.,Chavan, Abhijit P.
, p. 374 - 376 (2007/10/03)
A microwave-promoted Reformatsky reaction of aldehydes and ketones with ethyl bromoacetate, in the absence of solvent, using activated zinc metal and solid NH4Cl afforded the corresponding β-hydroxyesters in good to excellent yields.
Cyclic Ether Formation in Superacid Media
Carr, Graham,Whittaker, David
, p. 359 - 366 (2007/10/02)
The formation of ethers in superacids by interaction of a primary hydroxy group with a carbocation centre has been investigated by a study of cyclisation of suitable substrates, mainly 1-(2-hydroxyethyl)cyclohexanols to give hydrobenzofurans.Cyclisation traps thermodynamically stable ionic species, with rates of reaction dependent upon the size of the ether ring formed.Three- and four-membered ether rings were not formed, five-membered ether rings formed readily, the reaction being comparable in rate with a 1,2-methyl shift.Six-membered rings formed a little less readily and seven-membered rings less readily still, though a yield of 34 percent from a suitable substrate has been recorded.An unexpected feature of the reactions was their stereospecificity; in one case, this is believed to result from a methyl shift concerted with attack of the primary hydroxy group, the reaction proceeding through hindered transition state, in which methyl loss, probably as CH3+, competes with a 1,2-methyl shift.
