92527-70-3Relevant academic research and scientific papers
Practical hydroxymethylation of aldehydes and ketones via pinacol cross-coupling reactions with paraformaldehyde
Park, Jeonghan,Pedersen, Steven F.
, p. 2069 - 2080 (2007/10/02)
A general and practical method for the direct hydroxymethylation of aldehydes and ketones via pinacol cross-coupling with paraformaldehyde is described. The reaction is promoted by vanadium(II) ions which are conveniently generated from the reduction of VCl3(THF)3 with zinc dust. Excellent yields of terminal diols are obtained and stereoselective coupling is observed with some chiral aldehydes and ketones.
Reaction of 1,2-dioxetanes with heteroatom nucleophiles: Adduct formation by nucleophilic attack at the peroxide bond
Adam, Waldemar,Heil, Markus
, p. 5591 - 5598 (2007/10/02)
The reactions of 3,3-disubstituted 1,2-dioxetanes 1 with numerous heteroatom nucleophiles, e.g., R2NH, R3N, RSH, R2S, CN-, SCN-, Br-, Cl-, OH-, and O2*-, were investigated. Initial nucleophilic substitution at the sterically less hindered site of the dioxetane peroxide bond leads to addition, deoxygenation, and fragmentation products. The observed SN2 chemistry was substantiated with the dioxetane le because bromide ion displacement by the proximate alkoxide ion site afforded epoxide products. Thus, with anionic nucleophiles the epoxy alcohol 8c was obtained in appreciable amounts, and triethylamine and DABCO gave with 1c exclusively the alkoxyammonium epoxides 4c and 5c. Moreover, the labile alkoxysulfonium epoxide 6c was detected as an intermediate in the deoxygenation of 1c by diphenyl sulfide. From the reaction of 1b-d with secondary amines were isolated the hydroxylamine derivatives 2 and 3, and the cyanide and thiocyanate ions gave with 1c,d five-membered-ring insertion products, namely, the carbonates 9c,d and the cyclic sulfite 10c.
A NEW METHOD FOR THE HYDROXYMETHYLATION OF CARBONYL COMPOUNDS
Imamoto, Tsuneo,Takeyama, Toshiaki,Yokoyama, Masataka
, p. 3225 - 3226 (2007/10/02)
Benzyl chloromethyl ether reacts with carbonyl compounds in the presence of SmI2 to afford alcohols (I), which are subsequently subjected to hydrogenolysis to yield diols (II).
