17881-65-1Relevant articles and documents
Regioselectivity of Hydroxyl Radical Reactions with Arenes in Nonaqueous Solutions
Moores, Lee C.,Kaur, Devinder,Smith, Mathew D.,Poole, James S.
, p. 3260 - 3269 (2019/03/11)
The regioselectivity of hydroxyl radical addition to arenes was studied using a novel analytical method capable of trapping radicals formed after the first elementary step of reaction, without alteration of the product distributions by secondary oxidation processes. Product analyses of these reactions indicate a preference for o- over p-substitution for electron donating groups, with both favored over m-addition. The observed distributions are qualitatively similar to those observed for the addition of other carbon-centered radicals, although the magnitude of the regioselectivity observed is greater for hydroxyl. The data, reproduced by high accuracy CBS-QB3 computational methods, indicate that both polar and radical stabilization effects play a role in the observed regioselectivities. The application and potential limitations of the analytical method used are discussed.
Graphene oxide-bound electron-deficient tin(IV) porphyrin: a highly efficient and selective catalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazane
Zarrinjahan, Alireza,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj
, (2017/02/05)
The catalytic activity of graphene oxide-bound tetrakis(p-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [SnIV(TNH2PP)(OTf)2], in the trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) is reported. The prepared catalyst was characterized using inductively coupled plasma analysis, scanning electron microscopy, transmission electron microscopy, and Fourier transform infrared and diffuse reflectance UV–visible spectroscopies. This heterogeneous catalyst was used for selective trimethylsilylation of various alcohols and phenols with HMDS in short reaction times and high yields. Also, the catalyst is of high reusability and stability, in that it was recovered several times without loss of its initial activity. The chemoselectivity of this catalytic system in the silylation of primary alcohols in the presence of secondary and tertiary alcohols and also phenols was investigated.
Alkyl substituted [2.2]paracyclophane-1,9-dienes
Lidster, Benjamin J.,Kumar, Dharam R.,Spring, Andrew M.,Yu, Chin-Yang,Helliwell, Madeleine,Raftery, James,Turner, Michael L.
supporting information, p. 6079 - 6087 (2016/07/06)
[2.2]Paracyclophane-1,9-dienes substituted with n-octyl chains have been synthesised from the corresponding dithia[3.3]paracyclophanes using a benzyne induced Stevens rearrangement. The use of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate and tetra-n-butylammonium fluoride as the in situ benzyne source gave significantly improved yields over traditional sources of benzyne and enabled the preparation of n-octyl substituted [2.2]paracyclophane-1,9-dienes on a multi-gram scale.