707-07-3Relevant articles and documents
Anodic oxidation of dithiane carboxylic acids: A rapid and mild way to access functionalized orthoesters
Denis, Camille,Dobbs, Adrian P.,Garcia, Anthony D.,Goodall, Iain C. A.,Lam, Kevin,Leech, Matthew C.,Petti, Alessia
, p. 4000 - 4005 (2020/06/08)
A new electrochemical methodology has been developed for the preparation of a wide variety of functionalized orthoesters under mild and green conditions from easily accessible dithiane derivatives. The new methodology also offers an unprecedented way to access tri(fluorinated) orthoesters, a class of compound that has never been studied before. This provides the community with a rapid and general method to prepare libraries of functionalized orthoesters from simple and readily available starting materials.
A flexible Pinner preparation of orthoesters: The model case of trimethylorthobenzoate
Noe, Marco,Perosa, Alvise,Selva, Maurizio
, p. 2252 - 2260 (2013/09/24)
In the absence of additional solvents, a novel procedure was implemented for the synthesis of trimethylorthoesters through the Pinner reaction. At 5 °C, the reaction of both aliphatic and aromatic nitriles (RCN; R = Et, Bu, Ph) with a moderate excess of MeOH and gaseous HCl gave the corresponding imidate hydrochlorides [RC(NH)OR′·HCl] in excellent yields (>90%). At 25-65 °C, the methanolysis of alkyl imidate salts provided trimethylortho-propionate and valerate, while only traces of trimethylorthobenzoate (TMOB) were observed. However, the aromatic hydrochloride could be readily converted into the hydrogenphosphate salt [PhC(NH) OR′·H3PO4] which, in turn, underwent a selective (>80%) reaction with MeOH to produce TMOB in a 62% isolated yield. This allowed for an unprecedented Pinner-type synthesis of TMOB starting from benzonitrile, rather than from the highly toxic trichloromethylbenzene. Overall, remarkable improvements in safety and process intensification were achieved.
Metastable Ion Study of Organosilicon Compounds. Part III - Trimethoxyphenylsilane
Tajima, Susumu,Iida, Hiroyuki,Tobita, Seiji,Okada, Fumio,Tabei, Eiichi,Mori, Shigeru
, p. 441 - 445 (2007/10/02)
The unimolecular decomposition of trimethoxyphenylsilane (1) was investigated by mass-analysed ion kinetic energy (MIKE) spectrometry, deuterium-labelling studies and from high resolution data.The characteristic fragmentations of metastable molecular ion of 1 were losses of C6H6* and C7H7* with rearrangements.Almost complete H/D scrambling occurred in the molecular ion prior to these decompositions.The other important fragmentation routes corresponded to expulsion of CH3O* and C6H5*.These fragmentations were followed by consecutive elimination of an H2CO molecule, as commonly observed in the mass spectra of alkoxysilanes.In these fragmentation processes, H/D scrambling increased as the internal energy of the molecular ion was lowered.The fragmentations of 1 were compared with those of its carbon analogue, α,α,α-trimethoxytoluene.
