138142-60-6Relevant articles and documents
Rice husk: Introduction of a green, cheap and reusable catalyst for the protection of alcohols, phenols, amines and thiols
Shirini, Farhad,Akbari-Dadamahaleh, Somayeh,Mohammad-Khah, Ali,Aliakbar, Ali-Reza
, p. 164 - 170 (2014/03/21)
A mild, efficient and eco-friendly protocol for the chemoselective protection of benzylic and primary and less hindered secondary aliphatic alcohols and phenols as trimethylsilyl ethers and different types of amines as N-tert-butylcarbamates is developed using rice husk (RiH) as the catalyst. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols and amines with acetic anhydride. Easy work-up, relatively short reaction times, excellent yields and low cost, availability and reusability of the catalyst are the striking features of this methodology, which can be considered to be one of the best and general methods for the protection of alcohols, phenols, thiols and amines. In addition, the use of a green reagent in the above-mentioned reactions results in a reduction of environmental pollution and of the cost of the applied methods.
120. Stereoselective Ring Opening of Electronically Excited Cyclohexa-2,4-dienones: Cause and Effect
Quikert, Gerhard,Scherer, Stefan,Reichert, Dietmar,Nestler, Hans-Peter,Wennemers, Helma,Ebel, Andreas,Urbahns, Klaus,Wagner, Klaus,Michaelis, Klaus-Peter,Wiech, Gerhard,Prescher, Günter,Bronstert, Bernd,Freitag, Bernd-Jürgen,Wicke, Ilka,Lisch, Dietmar,Belik, Pavel,Crecelius, Thorsten,H?rstermann, Dirk,Zimmermann, Gottfried,Bats, Jan W.,Dürner, Gerd,Rehm, Dieter
, p. 1683 - 1772 (2007/10/03)
The two conformers of a cyclohexa-2,4-dienone with different substituents at C(6) on irradiation are believed to undergo ring opening stereospecifically affording a mixture of two configurationally isomeric diene-ketenes (and descendents thereof). Exceptions are generally found for those dienones with one C and one O substituent or even with two C substituents, if one of them carries a polar group at a site able to interact through space with the ring C=O group. In these cases, only one of the two anticipated diene-ketenes (and descendents thereof) is produced. A thorough investigation of the photochemistry of a series of structurally different cyclohexa-2,4-dienones on analytical as well as on preparative scale extends our mechanistic knowledge of the various routes from diene-ketenes into a variety of compound classes. Novel compound classes accessible to diene-ketenes are seven-membered carbocycles (by intramolecular aldolization of the zwitterion of appropriately substituted, transiently formed diene-(N,O)-ketene acetals) and βlactams (by Staudinger reaction).