ISSN:
1573-9171
Keywords:
synthesis
;
macrocyclic thiophenylene ketone
;
crystal structure
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract The side reaction of macrocyclization that occurs during the synthesis of poly-(1,4-phenylenesulfide ketone) by polycondensation of a 4,4-dihalobenzophenone with sodium sulfide was studied. It was found that the major product of this reaction is a cyclic trimer, cyclotris-(4,4"-thiodiphenylene ketone) (1). Despite the fact that ketone bridges are more rigid than sulfide bridges, the yield of the macrocycle is rather high, as it is in the synthesis of poly-(1,4-phenylenesulfide), and reaches 20% under high dilution conditions. The structure of 1 was investigated by X-ray diffraction analysis (R = 0.069 on 3138 reflections). Macrocycle 1 is strongly flattened in the crystal; the conformation observed is determined by the packing, since stereochemical analysis indicates high flexibility of the macrocycle. The solvate acetone molecules incorporated in the crystal are disordered, nevertheless, they are strongly fixed in the cavities and channels of the crystal structure.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00703700
Permalink
