26278-67-1Relevant articles and documents
Chemoselective and direct functionalization of methyl benzyl ethers and unsymmetrical dibenzyl ethers by using iron trichloride
Sawama, Yoshinari,Goto, Ryota,Nagata, Saori,Shishido, Yuko,Monguchi, Yasunari,Sajiki, Hironao
supporting information, p. 2631 - 2636 (2014/03/21)
Methyl and benzyl ethers are widely utilized as protected alcohols due to their chemical stability, such as the low reactivity of the methoxy and benzyloxy groups as leaving groups under nucleophilic conditions. We have established the direct azidation of chemically stable methyl and benzyl ethers derived from secondary and tertiary benzyl alcohols. The present azidation chemoselectively proceeds at the secondary or tertiary benzylic positions of methyl benzyl ethers or unsymmetrical dibenzyl ethers and is also applicable to direct allylation, alkynylation, and cyanation reactions, as well as the azidation. The present methodologies provide not only a novel chemoselectivity but also the advantage of shortened synthetic steps, due to the direct process without the deprotection of the methyl and benzyl ethers. Ethers exchanged: Methyl and benzyl ethers are chemically stable and generally tolerant under nucleophilic substitution conditions. Iron-catalyzed direct functionalizations (e.g., azidation, allylation, alkynylation, and cyanation) of methyl and benzyl ethers derived from secondary and tertiary benzyl alcohols were established with excellent regioselectivities (see scheme; PG: protecting group; Bn: benzyl; Nu: nucleophile; TMS: trimethylsilyl). Copyright
METHOXYMETHYL METHYL SULFATE - A NEW REAGENT FOR THE FUNCTIONALIZATION OF OLEFINS AND ACETYLENES
Lebedev, M. Yu.,Balenkova, E. S.
, p. 1214 - 1219 (2007/10/02)
The reaction of methylenecyclobutane, styrene, 1-hexene, and phenyl- and diphenylacetylenes with methoxymethyl methyl sulfate, generated in situ from methylal and sulfur trioxide, takes place as conjugate addition of the methoxymethyl and methyl sulfate groups and leads to the respective alkoxymethyl sulfates in the case of olefins and vinyl methyl sulfates in the case of acetylenes.The high reactivity of the obtained compounds in reactions with nucleophiles was used for the synthesis of diethers, unsaturated ethers, and acetoxy and α,β-unsaturated ketones.
DETERMINATION OF OPTIMAL CONDITIONS FOR OBTAINING 1, 3-DIMETHOXY-1-PHENYLPROPANE BY ADDITION OF METHYLAL TO STYRENE.
Brudnik,Akhmatdinov,Kantor,Rakhmankulov
, p. 1697 - 1701 (2007/10/02)
In this work the reaction of styrene with methylal was investigated in order to gain insight into the reaction and determine the conditions for obtaining acceptable yields of 1, 3-dimethoxy-1-phenylpropane. In a previous work boron trifluoride was recomme