para-Selective chlorination of cresols and m-xylenol using sulfuryl chloride in the presence of poly(alkylene sulfide)s

References

• Ullmann’s encyclopedia of industrial chemistry. 6th ed. Weinheim: Wiley-VCH; 1998.
   Google Scholar
• World Health Organization, Stuart MC, Kouimtzi M, Hill SR, editors. WHO Model Formulary 2008. World Health Organization; 2009.
   Google Scholar
• Griffiths C, Barker J, Bleiker T, et al. Rook's textbook of dermatology. 9th ed. Oxford: John Wiley & Sons; 2017.
   Google Scholar
• Digison MB. A review of anti-septic agents for pre-operative skin preparation. Plast Surg Nurs. 2007;27:185–189. doi: 10.1097/01.PSN.0000306182.50071.e2
   PubMedGoogle Scholar
• Mahon CR, Lehman DC, Manuselis G. Textbook of diagnostic microbiology. 5th ed. Oxford: Elsevier Health Sciences; 2014.
   Google Scholar
• Frébortová J. Determination of chlorophenols in soils by a method involving alkaline extraction and solid-phase preconcentration prior to high-performance liquid chromatography. Biosci Biotech Biochem. 1995;59:1930–1932. doi: 10.1271/bbb.59.1930
   PubMed Web of Science ®Google Scholar
• Ogata Y, Kimura M, Kondo Y, et al. Orientation in the chlorination of phenol and of anisole with sodium and t-butyl hypochlorites in various solvents. J Chem Soc Perkin Tans. 1984;2(3):451–453. doi: 10.1039/p29840000451
   Google Scholar
• De la Mare PBD. Electrophilic halogenation. Cambridge: Cambridge University Press; 1976.
   Google Scholar
• Gibson GP. CLXXXV – the monochloro-derivatives of m-cresol. J Chem Soc. 1926;129:1424–1428. doi: 10.1039/JR9262901424
   Google Scholar
• Gnaim JM, Sheldon RA. Shape-selective para-chlorination of phenol using sulfuryl chloride with the aid of microporous catalysts. Tetrahedron Lett. 2004;45:9397–9399. doi: 10.1016/j.tetlet.2004.10.109
   Web of Science ®Google Scholar
• Xiong X, Yeung Y-Y. Ammonium salt-catalyzed highly practical ortho-selective monohalogenation and phenylselenation of phenols: scope and applications. ACS Catal. 2018;8:4033–4043. doi: 10.1021/acscatal.8b00327
   Web of Science ®Google Scholar
• Nahide PD, Ramadoss V, Juárez-Ornelas KA, et al. In situ formed I(III)-based reagent for the electrophilic ortho-chlorination of phenols and phenol ethers: the use of PIFA-AlCl3 system. Eur J Org Chem. 2018: 485–493. doi: 10.1002/ejoc.201701399
   Web of Science ®Google Scholar
• Xin H, Yang S, An B, et al. Selective water-based oxychlorination of phenol with hydrogen peroxide catalysed by manganous sulfate. RSC Adv. 2017;7:13467–13472. doi: 10.1039/C7RA00319F
   Web of Science ®Google Scholar
• Maddox SM, Dinh AN, Armenta F, et al. A practical Lewis base catalyzed electrophilic chlorination of arenes and heterocycles. Org Lett. 2016;18:5476–5479. doi: 10.1021/acs.orglett.6b02650
   PubMed Web of Science ®Google Scholar
• Denmark SE, Beutner GL. Lewis base catalysis in organic synthesis. Angew Chem Int Ed Engl. 2008;47:1560–1638. doi: 10.1002/anie.200604943
   PubMed Web of Science ®Google Scholar
• Smith K, Butters M, Nay B. Highly para-selective mono-chlorination of aromatic compounds under mild conditions by t-butyl hypochlorite in the presence of zeolites. Synthesis (Stuttgart). 1985;(12):1157–1158. doi: 10.1055/s-1985-31462
   Web of Science ®Google Scholar
• Smith K, James DM, Matthews I, et al. Selective para-bromination of phenols via a regenerable polymer-bound tetralkylammonium tribromide. J Chem Soc Perkin Trans. 1992;1:1877–1878. doi: 10.1039/p19920001877
   Google Scholar
• Smith K, He P, Taylor A. Selective para-bromination of phenyl acetate under the control of zeolites, bases, acetic anhydride or metal acetates in the liquid phase. Green Chem. 1999;1:35–38. doi: 10.1039/a808242a
   Web of Science ®Google Scholar
• Smith K, El-Hiti GA, Hammond MEW, et al. Highly efficient and selective electrophilic and free radical catalytic bromination reactions of simple aromatic compounds in the presence of reusable zeolites. J Chem Soc, Perkin Trans. 2000;1(16):2745–2752. doi: 10.1039/b002157l
   Google Scholar
• Smith K, El-Hiti GA. Regioselective electrophilic aromatic substitution reactions over reusable zeolites. Curr Org Chem. 2006;10:1603–1625. doi: 10.2174/138527206778249685
   Web of Science ®Google Scholar
• Smith K, El-Hiti GA. Use of zeolites for green and para-selective electrophilic aromatic substitution reactions. Green Chem. 2011;13:1579–1608. doi: 10.1039/c0gc00689k
   Web of Science ®Google Scholar
• Bugnet EA, Brough AR, Greatrex R, et al. On the para-selective chlorination of ortho-cresol. Tetrahedron. 2002;58:8059–8065. doi: 10.1016/S0040-4020(02)00996-1
   Web of Science ®Google Scholar
• Watson WD. Regioselective para chlorination of activated aromatic compounds. J Org Chem. 1985;50:2145–2148. doi: 10.1021/jo00212a029
   Web of Science ®Google Scholar
• Watson WD. The regioselective para chlorination of 2-methylphenol. Tetrahedron Lett. 1976;17:2591–2594. doi: 10.1016/S0040-4039(00)91742-8
   Google Scholar
• Watson WD. Chlorination with sulfuryl chloride. United States Patent US 3,920,757A. Chem Abstr. 1976;84:43612.
   Google Scholar
• Smith K, Tzimas M, Brown CM, et al. Dialkyl sulfides as selective catalysts for the chlorination of phenols. Sulfur Lett. 1999;22:89–101.
   Google Scholar
• Smith K, Tzimas M, Brown CM, et al. Dithia-alkanes and modified Merrifield resins as selective catalysts for the chlorination of phenols. Sulfur Lett. 1999;22:103–123.
   Google Scholar
• Smith K, Al-Zuhairi AJ, El-Hiti GA, et al. Comparison of cyclic and polymeric disulfides as catalysts for the regioselective chlorination of phenols. J Sulfur Chem. 2015;36:74–85. doi: 10.1080/17415993.2014.965170
   Web of Science ®Google Scholar
• Smith K, Al-Zuhairi AJ, Elliott MC, et al. Regioselective synthesis of important chlorophenols in the presence of methylthioalkanes with remote SMe, OMe or OH substituents. J Sulfur Chem. 2018;39:607–621. doi: 10.1080/17415993.2018.1493111
   Web of Science ®Google Scholar
• Smith K, El-Hiti GA, Al-Zuhairi AJ. The synthesis of polymeric sulfides by reaction of dihaloalkanes with sodium sulfide. J Sulfur Chem. 2011;32:521–531. doi: 10.1080/17415993.2011.616589
   Web of Science ®Google Scholar
• Smith K, Hegazy AS, El-Hiti GA. The use of polymeric sulfides as catalysts for the para-regioselective chlorination of phenol and 2-chlorophenol. J Sulfur Chem. 2020;41:1–12. doi: 10.1080/17415993.2019.1688815
   Web of Science ®Google Scholar