33641-39-3Relevant articles and documents
X-ray investigations of sulfur-containing fungicides. III. Intramolecular forces governing the conformation of a novel orthorhombic polymorph of benzoylmethyl phenyl sulfone, benzoylmethyl 4-chlorophenyl sulfone and benzoylphenylmethyl phenyl sulfone
Wolf
, p. 806 - 814 (2001)
The crystal and molecular structures of three β-ketosulfones: benzoylmethyl phenyl sulfone (I), benzoylmethyl 4-chlorophenyl sulfone (II) and benzoylphenylmethyl phenyl sulfone (III) have been investigated using X-ray analysis and quantum mechanics ab initio calculations. Compound (I) crystallizes in the monoclinic and orthorhombic crystal systems. The crystal structure of the orthorhombic polymorph has not been reported previously. At room temperature and in the presence of daylight the pale yellow orthorhombic crystals undergo transformation to the stable colourless monoclinic polymorph. Hyperconjugative σ(S-C1) - π*(C2=O3) and σ*(S-C1) -π(C2=O3) stabilization energies in benzoylmethyl phenyl sulfones are highly dependent on the central dihedral angle α: S-C1-C2=O3 and arc largest for a gauche arrangement, as found in both crystal forms of (I). The electron density distribution in all compounds (I), (II) and (III) is significantly affected by interactions of oxygen lone pairs with non-bonding orbitals of the adjacent S-C1 and C1-C2 bonds. The latter effect is responsible for back-donation of the electron density from O atoms towards the central part of the molecule.
Efficient conversion of sulfones into β-keto sulfones by N-acylbenzotriazoles
Katritzky, Alan R.,Abdel-Fattah, Ashraf A. A.,Wang, Mingyi
, p. 1443 - 1446 (2007/10/03)
Acyclic sulfones 4a-f and alicyclic sulfone 7 react with readily available N-acylbenzotriazoles 3a-g (derived from aliphatic, aromatic, and heteroaromatic carboxylic acids) to provide the corresponding β-keto sulfones 5a-n and 8a-c, respectively, in good
