41105-40-2Relevant academic research and scientific papers
Optimization of the synthesis of phenanthrene-2- and -3-sulfonyl chlorides
Russkikh,Khokhrina,Shelkovnikov
experimental part, p. 547 - 551 (2012/06/29)
Sulfonation of phenanthrene with sulfuric acid, followed by neutralization with sodium hydroxide, gave a mixture of isomeric sodium phenanthrenesulfonates in an overall yield of 83%. Sodium phenanthrene- 2-, -3-, and -9-sulfonates were isolated in 17, 43, and 4% yield, respectively. Sulfonation of phenanthrene with ClSO3H or SO3 did not improve the yields of phenanthrene-2- and -3-sulfonic acids. Treatment of sodium phenanthrene-2- and -3-sulfonates with PCl5-POCl3 or SOCl2-DMF afforded the corresponding sulfonyl chlorides in 89 and 87 or 69 and 70% yield, respectively. Pure phenanthrene-2- and -3-sulfonyl chlorides were also synthesized in 27 and 51% yield by reaction of a mixture of 2- and 3-sulfonates with PCl5-POCl3. Pleiades Publishing, Ltd., 2012.
The sulfonation of aromatic and heteroaromatic polycyclic compounds
Katritzky, Alan R.,Kim, Myong Sang,Fedoseyenko, Dmytro,Widyan, Khalid,Siskin, Mike,Francisco, Manuel
experimental part, p. 1111 - 1114 (2009/04/07)
Relative reactivities of a series of polycyclic carbo- and heteroaromatic compounds to sulfonation by sulfur trioxide in nitrobenzene are measured and discussed. The results show the following reactivity in decreasing order: indole, carbazole, pyrene, perylene, naphthalene, phenanthrene, benzene, benzothiophene, and dibenzothiophene.
Sulfonation of a Series of Bromo- and Methylphenanthrenes with Sulfur Trioxide
Cerfontain, Hans,Koeberg-Telder, Ankie,Laali, Khosrow,Lambrechts, Hans J. A.
, p. 4069 - 4075 (2007/10/02)
The sulfonation of a series of methylphenanthrenes (MPs) and two bromophenanthrenes with SO3 in nitromethane has been studied at O deg C.From the substitution pattern it is evident that steric factors play an important role.Substitution of the 4- and 5-H peri to the methyl does not occur, and that ortho to the 9-methyl is severely reduced.Provided that allowance is made for the steric factors, the positional order of substitution for monosulfonation of a given (methyl)phenanthrene is in agreement with that predicted by the localization energies, calculated by a simple Hueckel MO treatment.The position of substitution of the second sulfo group is governed by two factors, viz., the positional localization energies of the starting MP (which will lead to symmetrical disulfonic acids) and the directing effect of the first (pyro)sulfonic acid group (leading to asymmetrical disulfonic acids).The latter factor is only apparent when the difference in localization energy for the positions of substitution under question of the starting MP are not too large.The formation of disulfonic acids with 2,4,5,7- and 3,4,5,6-TMP when 1 equiv of SO3 is used is ascribed to a mixing-disguised substrate selectivity, as a result of the very high reactivities of both the given TMP and its monosulfonic acid toward SO3.
