36626-52-5Relevant academic research and scientific papers
Chemoselective Deoxygenation of 2° Benzylic Alcohols through a Sequence of Formylation and B(C6F5)3-Catalyzed Reduction
Oestreich, Martin,Richter, Sven C.
supporting information, p. 2103 - 2106 (2021/07/22)
A sequence of formylation and B(C6F5)3-catalyzed reduction of the resulting formate with Et3SiH enables the chemoselective deoxygenation of secondary benzylic alcohols. Primary benzylic and tertiary non-benzylic alcohols are not reduced by this protocol. The formyl group fulfills a double role as activator and self-sacrificing protecting group. The deoxygenation of these formates is fast and can be carried out in the presence of other potentially reducible groups. Neighboring-group participation was found in the deoxygenation of certain diol motifs.
The Reaction of Olefins with Chloroalkoxyalkanes and Formic Acid in Ether
Nishiura, Kazuo,Tagano, Tsutomu,Wada, Yasuo,Tanimoto, Shigeo,Okano, Masaya
, p. 1376 - 1380 (2007/10/02)
The reaction of olefins with chloromethoxymethane (CMM) and excess formic acid in ether, in the presence of ZnCl2 or HgCl2, affored mainly four products, 1-chloro- and 1-formyloxy-2-(formyloxymethyl)alkanes, and 3,5-dialkyl-4-chloro- and 3,5-dialkyl-4-(formyloxy)tetrahydropyrans, in various yields.In the case of styrene, the chief products were limited to the former two.Similar products were obtained from 1-chloro-1-ethoxyethane(CEE), but their yields were quite low.
