76965-78-1Relevant articles and documents
Alcohols as electrophiles: Iron-catalyzed Ritter reaction and alcohol addition to alkynes
Jefferies, Latisha R.,Cook, Silas P.
supporting information, p. 4204 - 4207 (2014/06/09)
A simple, iron-based catalytic system allows for a straightforward method for the synthesis of primary, secondary, and tertiary amides. The system also allows the addition of benzyl alcohols across phenylacetylene to produce substituted phenyl ketones. This transformation improves and expands the substrate scope beyond that previously reported and proceeds under mild reaction conditions, tolerating air and moisture.
Metal-free conversion of methane and cycloalkanes to amines and amides by employing a borylnitrene
Bettinger, Holger F.,Filthaus, Matthias,Bornemann, Holger,Oppel, Iris M.
experimental part, p. 4744 - 4747 (2009/02/06)
(Chemical Equation Presented) C-H insertion: Borylnitrenes, which are generated in situ by photoylsis of azides, convert unactivated alkanes by intermolecular C-H insertion into aminoboranes (see scheme), which in turn can be reacted further to give amines or amides. The boryl group serves two purposes: it converts the nitrene into a highly reactive BN vinylidene analogue, and it is easily cleaved from the product.
Reactions of Thianthrene Cation Radical with Acyclic and Cyclic Alcohols
Shine, Henry J.,Yueh, Wang
, p. 3553 - 3559 (2007/10/02)
Thianthrene cation radical perchlorate (Th(.+)*ClO4(-)) reacted readily with cycloalkanols (C5, C7, C8, and C12), alkan-2-ols (C3, C5, C6, and C8), 3-hexanol, neopentyl alcohol, a number of benzyl alcohols, dl- and (S)-1-phenylethanol, cyclopentyl- and cyclohexylmethanols, the exo- and endo-borneols, and norborneols.Reactions were carried out with an excess of the alcohol in acetonitrile solution containing 2,6-di-tert-butyl-4-methylpyridine.Products were alkenes, ethers, and N-substituted acetamides, depending on the structure of the alcohol.Thianthrene (Th) and its 5-oxide (ThO) were formed in equal amounts.The sum of amounts of products from the alcohol was equal to the amount of ThO.All reactions are interpretable on the basis of the ultimate formation and further reactions of a 5-alkoxythianthreniumyl ion (ROTh(+)).The predominant formation of nortricyclene from the norborneols is striking and is discussed.Swern-Moffatt-type oxidations of the alcohols were not observed.
