Optimization of the synthesis of phenanthrene-2-and-3-sulfonyl chlorides

Optimization of the synthesis of phenanthrene-2-and-3-sulfonyl chlorides Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2012, Volume: 48, Number: 4, Pages: 547-551 Pages count : 5 DOI: 10.1134/S1070428012040148

Authors

Russkikh V.V. ¹ , Khokhrina E.A. ¹ , Shelkovnikov V.V. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Div, Novosibirsk 630090, Russia

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.

Russkikh V.V. , Khokhrina E.A. , Shelkovnikov V.V.
Optimization of the synthesis of phenanthrene-2-and-3-sulfonyl chlorides
Russian Journal of Organic Chemistry. 2012. V.48. N4. P.547-551. DOI: 10.1134/S1070428012040148 WOS Scopus РИНЦ

Русских В.В. , Хохрина Е.А. , Шелковников В.В.
Оптимизация синтеза фенантрен-2- и -3-сульфонилхлоридов
Журнал органической химии (RUSS J ORG CHEM+). 2012. Т.48. №4. С.549-553. РИНЦ

Published print:	Apr 1, 2012
Published online:	May 5, 2012

Web of science	WOS:000303682800014
Scopus	2-s2.0-84862086949
Elibrary	17990306
OpenAlex	W2146323792