Breakthrough in the α-Perchlorination
of Acyl Chlorides

Franco Bellesia; Francesca D’Anna; Fulvia Felluga; Vincenzo Frenna; Franco Ghelfi; Andrew F. Parsons; Federico Reverberi; Domenico Spinelli

doi:10.1055/s-0031-1289678

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Synthesis 2012(4): 605-609
DOI: 10.1055/s-0031-1289678

PAPER

Breakthrough in the α-Perchlorination of Acyl Chlorides

Franco Bellesia^a, Francesca D’Anna^b, Fulvia Felluga^c, Vincenzo Frenna^b, Franco Ghelfi*^a, Andrew F. Parsons^d, Federico Reverberi*^a, Domenico Spinelli^e
^a Dipartimento di Chimica, Università degli Studi di Modena e Reggio Emilia, Via Campi 183, 41125 Modena, Italy
Fax: +39(59)373543; e-Mail: franco.ghelfi @unimore.it;
^b Dipartimento di Chimica Organica ‘E. Paternò’, Università degli Studi di Palermo, Viale delle Scienze-Parco D’Orleans II, 90128 Palermo, Italy
^c Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Trieste, Via L. Giorgeri 1, 34127 Trieste, Italy
^d Department of Chemistry, University of York, Heslington, York YO10 5DD, UK
^e Dipartimento di Chimica ‘G. Ciamician’, Università degli Studi di Bologna, Via Selmi 2, 40126 Bologna, Italy

Further Information

Publication History

Received 25 October 2011
Publication Date:
26 January 2012 (online)

Abstract
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Abstract

The preparation of α-perchloroacyl chlorides, from reaction of the corresponding unfunctionalized acyl halides with chlorine, was efficiently achieved under base-catalysis, using a tetraalkylammonium chloride as catalyst. The process is solvent-free and the procedure is easy, inexpensive, and suitable for scale-up.

Key words

acyl chlorides - halogenation - chlorine - base catalysis - 2,2-dichloroacyl chlorides

References

1 Westbrooksss Westbrook JA. Schaus SE. Science of Synthesis Vol. 20a: Georg Thieme Verlag; Stuttgart: 2006. p.371

Google Scholar
For reactions at the C=O site, see, for example:
2a Forti L. Ghelfi F. Munari F. Pagnoni UM. Tetrahedron 1995, 51: 12285

Google Scholar
2b Forti L. Ghelfi F. Grandi R. Libertini E. Pagnoni UM. Synth. Commun. 1996, 26: 3517

Google Scholar
2c Lindner E. Steinwand M. Hoehne S. Angew. Chem., Int. Ed. Engl. 1982, 94: 355

Google Scholar
2d Larcheveque M. Perriot P. Petit Y. Synthesis 1983, 297

Google Scholar
2e Bratchanskii PE, Moreiko MN, and Begunova OA. inventors; SU 296,407.

Google Scholar
2f Nouri-Bimorghi R. Bull. Soc. Chim. Fr. 1965, 3178

Google Scholar
For reactions at the CCl₂ site, see for example:
3a Watanabe M, Nishimiya T, and Fukui A. inventors; JP 2008,184,411.

Google Scholar
3b Mathieu V, Janssens F, and Franklin J. inventors; WO 2002,012,160.

Google Scholar
3c Bratchanskii PE. Komissarova GG. Khim.-Farm. Zh. 1986, 20: 606

Google Scholar
3d Lingens F. Sprössler B. Justus Liebigs Ann. Chem. 1967, 709: 173

Google Scholar
3e Burbaum BW, Li C, and Matcham GW. inventors; US 5,424,454.

Google Scholar
3f Najzarek Z. inventors; PL 134,974.

Google Scholar
3g Lee L.-H, and Ranck DE. inventors; US 3,524,880.

Google Scholar
3h Concellón JM. Huerta M. Tetrahedron Lett. 2004, 45: 4665

Google Scholar
3i Lambert C. Caillaux B. Viehe HG. Tetrahedron 1985, 41: 3331

Google Scholar
For reaction across the CCl₂C=O, see for example:
4a Himbert G. Kosack S. Chem. Ber. 1988, 121: 2157

Google Scholar
4b Speziale AJ. Smith LR. J. Am. Chem. Soc. 1962, 84: 1868

Google Scholar
4c Pirrung MC. De Amicis CV. Tetrahedron Lett. 1988, 29: 159

Google Scholar
5a Casolari R. Felluga F. Frenna V. Ghelfi F. Pagnoni UM. Parsons AF. Spinelli D. Tetrahedron 2011, 67: 408

Google Scholar
5b Bregoli M. Felluga F. Frenna V. Ghelfi F. Pagnoni UM. Parsons AF. Petrillo G. Spinelli D. Synthesis 2011, 1267

Google Scholar
5c Feldman KS. Ngernmeesri P. Org. Lett. 2005, 7: 5449

Google Scholar
5d De Buyck L. Cagnoli R. Ghelfi F. Merighi G. Mucci A. Pagnoni UM. Parsons AF. Synthesis 2004, 1680

Google Scholar
5e Benedetti M. Forti L. Ghelfi F. Pagnoni UM. Ronzoni R. Tetrahedron 1997, 53: 14031

Google Scholar
5f Forti L. Ghelfi F. Libertini E. Pagnoni UM. Soragni E. Tetrahedron 1997, 53: 17761

Google Scholar
5g Hayes TK. Villani RS. Weinreb M. J. Am. Chem. Soc. 1988, 110: 5533

Google Scholar
6a Rodríguez-Solla H. Concellón C. Blanco EG. Sarmiento JI. Díaz P. Soengas RG. J. Org. Chem. 2011, 76: 5461

Google Scholar
6b Concellón JM. Rodríguez-Solla H. del Amo V. Díaz P. Synthesis 2009, 2634

Google Scholar
6c Condon S. Zou C. Nédélec J.-Y. J. Organomet. Chem. 2006, 691: 3245

Google Scholar
6d Benincasa M. Forti L. Ghelfi F. Libertini E. Pagnoni UM. Synth. Commun. 1996, 26: 4113

Google Scholar
6e Normant H. J. Organomet. Chem. 1975, 100: 189

Google Scholar
6f Villieras J. Perriot P. Bourgain M. Normant J.-F.
J. Organomet. Chem. 1975, 102: 129

Google Scholar
6g Villieras J. Disnar J.-R. Normant J.-F. J. Organomet. Chem. 1974, 81: 281

Google Scholar
6h Villieras J. Disnar J.-R. Normant J.-F.
J. Organomet. Chem. 1974, 81: 295

Google Scholar
7a Roncaglia F. Stevens CV. Ghelfi F. Van der Steen M. Pattarozzi M. De Buyck L. Tetrahedron 2009, 65: 1481

Google Scholar
7b Ghelfi F. Pattarozzi M. Roncaglia F. Giangiordano V. Parsons AF. Synth. Commun. 2010, 40: 1040

Google Scholar
7c Bellesia F. Danieli C. De Buyck L. Galeazzi R. Ghelfi F. Mucci A. Orena M. Pagnoni UM. Parsons AF. Roncaglia F. Tetrahedron 2006, 62: 746

Google Scholar
7d Mascal M. Moody CJ. Slawin AMZ. Williams DJ. J. Chem. Soc., Perkin Trans. 1 1992, 823

Google Scholar
7e Hirofumi M. Hiroyoshi O. Tadao I. Takehisa K. Heterocycles 1998, 49: 343

Google Scholar
7f Wolff HP, Heerdt R, Hübner M, Kühnle H, and Schmidt FH. inventors; US 4,425,360.
8a Hiraoka T, and Sugimura Y. inventors; JP 51,001,488.
8b Patel JR, Gopalkuma C, Sheth GS, Shah SR, Mandhane SN, Chitturi TR, and Thennati R. inventors; WO 2007,099,548.
8c Leasure JK. J. Agric. Food Chem. 1964, 12: 40

Google Scholar
8d Chen X. Xu W. Drugs Future 2006, 31: 875

Google Scholar
9a Plaum MJM, and Boesten WHJ. inventors; EP 796,853.
9b D’Anna F. Frenna V. Ghelfi F. Macaluso G. Marullo S. Spinelli D. J. Phys. Chem. A 2010, 114: 10969

Google Scholar
9c Rozen S. Hebel D. J. Org. Chem. 1990, 55: 2621

Google Scholar
9d Kibal’nikova RI. Shreibert AI. Khim. Khim. Tekhnol. (Lvov) 1968, 340

Google Scholar
10a Godfrey JD. Fox RT. Buono FG. Gougoutas JZ. Malley MF. J. Org. Chem. 2006, 71: 8647

Google Scholar
10b Imashiro R. Kuroda T. J. Org. Chem. 2003, 68: 974

Google Scholar
10c Black TH. McDermott TS. J. Chem. Soc., Chem. Commun. 1991, 184

Google Scholar
10d Shono T. Kise N. Tanabe T.
J. Org. Chem. 1988, 53: 1364

Google Scholar
10e Hayon A.-F. Fehrentz J.-A. Chapleur Y. Castro B. Bull. Soc. Chim. Fr. 1983, II-207

Google Scholar
10f Villieras J. Disnar JR. Perriot P. Normant JF. Synthesis 1975, 524

Google Scholar
10g Castro B. Villieras J. Ferracutti N. Bull. Soc. Chim. Fr. 1969, 3521

Google Scholar
10h Timmler H. Wegler R. Chem. Ber. 1967, 100: 2362

Google Scholar
11a Mume E. Munslow IJ. Kälström K. Andersson PG. Collect. Czech. Chem. Commun. 2007, 72: 1005

Google Scholar
11b Nakano T. Shimada Y. Sako R. Kayama M. Matsumoto H. Nagai Y. Chem. Lett. 1982, 1255

Google Scholar
11c Boutevin B. Piétrasanta Y. El Sarraf T. Makromol. Chem. 1982, 183: 2359

Google Scholar
11d Martin P. Steiner E. Bellu D. Helv. Chim. Acta 1980, 63: 1947

Google Scholar
11e Sorba J. Lefort D. Bull. Soc. Chim. Fr. 1975, 1861

Google Scholar
11f Kharasch MS. Hurry WH. Jensen EV. J. Am. Chem. Soc. 1945, 67: 1626

Google Scholar
12a Tato F. Reboul V. Metzner P. J. Org. Chem. 2008, 73: 7837

Google Scholar
12b Craig D. King NP. Mountford DM. Chem. Commun. 2007, 1077

Google Scholar
12c Palomo C. Miranda JI. Lynden A. J. Org. Chem. 1996, 61: 9196

Google Scholar
12d Malherbe R. Rist G. Belluš D. J. Org. Chem. 1983, 48: 860

Google Scholar
12e Baldwin JK. Walker JA. J. Chem. Soc., Chem. Commun. 1973, 117

Google Scholar
13a Frank-Neumann M. Miesch M. Kempf H. Tetrahedron 1987, 43: 853

Google Scholar
13b McDonald RN. Cousins RC. J. Org. Chem. 1980, 45: 2976

Google Scholar
14a Wessjohann L. Giller K. Zuck B. Scattebøl L. de Meijere A. J. Org. Chem. 1993, 58: 6442

Google Scholar
14b Migron Y. Blum J. Bar-Tana J. Tetrahedron 1987, 43: 361

Google Scholar
15a Shakhnazaryan GM. Bayatyan BE. Zh. Prikl. Khim. 1979, 52: 2307

Google Scholar
15b Shakhnazaryan GM. Garibyan VA. Dangyan MT. Armyan. Khim. Zh. 1968, 21: 962

Google Scholar
15c Vasil’eva EI. Freídlina RK. Izv. Akad. Nauk SSSR., Otd. Khim. Nauk 1960, 1215

Google Scholar
16 Bellesia F. Boni M. Ghelfi F. Pagnoni UM. Tetrahedron Lett. 1994, 35: 2961

Google Scholar
17a Englin AL, Sergeev EV, and Emel’yanova KN. inventors; SU 112,346.
17b Migaichuk IV. Khaskin IG. Zh. Prikl. Khim. 1982, 55: 2066

Google Scholar
18a De Buyck L. Casaert F. De Lepeleire C. Schamp N. Bull. Soc. Chim. Belg. 1988, 97: 525

Google Scholar
18b Bellesia F. De Buyck L. Ghelfi F. Synlett 2000, 146

Google Scholar
18c Bellesia F. De Buyck L. Ghelfi F. Pagnoni UM. Strazzolini P. Synth. Commun. 2004, 34: 1473

Google Scholar
19 Watson HB. Chem. Rev. 1930, 7: 173

Google Scholar
20a Salmi T. Mäki-Arvela P. Paatero E. Byggningsbacka R. J. Chem. Technol. Biotechnol. 2000, 75: 89

Google Scholar
20b Mäki-Arvela P. Salmi T. Paatero E. Sjöholm R. Ind. Eng. Chem. Res. 1995, 34: 1976

Google Scholar
20c Paatero E. Salmi T. Fagerstolt K. Ind. Eng. Chem. Res. 1992, 31: 2425

Google Scholar
20d Stevens C. De Buyck L. De Kimpe N. Tetrahedron Lett. 1998, 39: 8739

Google Scholar
20e Ogata Y. Sugimoto T. Inaishi M. Bull. Soc. Chem. Jpn. 1979, 52: 255

Google Scholar
20f Harpp DN. Bao LQ. Black CJ. Gleason JG. Smith RA. J. Org. Chem. 1975, 40: 3420

Google Scholar
20g Rodin RL. Gershon H. J. Org. Chem. 1973, 38: 3919

Google Scholar
20h Ogata Y. Matsuyama K. Tetrahedron 1970, 26: 5929

Google Scholar
21a Fooladi MM. inventors; US 3,882,045.
21b Sasaki R, Fuseda M, Tanaka J, and Tawara T. inventors; JP 45,039,804.
21c Murayama H, Kubo K, and Omi A. inventors; JP 43,017,164.
21d Schlecht H, Albers H, and Aurnhammer R. inventors; DE 1,133,710.
21e . inventors; GB 805,260.
22a Bardin VV. Furin GG. Yakobson GG. Zh. Org. Khim. 1984, 20: 567

Google Scholar
22b Yagupol’skii LM. Milevskaya VB. Matyushecheva GI. Zh. Org. Khim. 1975, 11: 2580

Google Scholar
23a Eilingsfeld H. Seefelder M. Weidinger H. Chem. Ber. 1963, 96: 2899

Google Scholar
23b von Braun J. Jostes F. Münch W. Justus Liebigs Ann. Chem. 1926, 453: 113

Google Scholar
23c Smeykal K. Pallutz H. Chem. Tech. (Leipzig, Ger.) 1963, 15: 654

Google Scholar
24a Treibs W. Zimmerman G. Chem. Ber. 1957, 90: 1146

Google Scholar
24b Shevchenko VI. Nizhnikova EE. Bodnarchuk ND. Kornuta PP. Zh. Obshch. Khim. 1967, 37: 1358

Google Scholar
25a Bellesia F. De Buyck L. Ghelfi F. Pagnoni UM. Parsons AF. Pinetti A. Synthesis 2003, 2173

Google Scholar
25b Bellesia F. De Buyck L. Ghelfi F. Libertini E. Pagnoni UM. Roncaglia F. Tetrahedron 2000, 56: 7507

Google Scholar
26a Pedzisa L. Hay BP. J. Org. Chem. 2009, 74: 2554

Google Scholar
26b Pilepić V. Jacobušić C. Vikić-Topić D. Uršić S. Tetrahedron Lett. 2006, 47: 371

Google Scholar
26c Abraham MH. Zhao YH. J. Org. Chem. 2004, 69: 4677

Google Scholar
26d Bordwell FG. Acc. Chem. Res. 1988, 21: 456

Google Scholar
26e Dehmlow EV. Thieser R. Tetrahedron Lett. 1985, 26: 297

Google Scholar
26f Hist J. Onyido I. J. Chem. Soc., Perkin Trans. 2 1984, 711

Google Scholar
27a Meng Q. Thibblin A. J. Chem. Soc., Perkin Trans. 2 1999, 1397

Google Scholar
27b Pews RG. Gall JA. J. Org. Chem. 1994, 59: 6783

Google Scholar
27c Fu Y. Xie D. Wang R. Wang C. Zhang X. Wang Q. Chem. Res. Chin. Univ. 1992, 8: 53

Google Scholar
27d Halpern M. Zahalka HA. Sasson Y. Rabinovitz M. J. Org. Chem. 1985, 50: 5088

Google Scholar
27e Biale G. Parker AJ. Smith SG. Stevens IDR. Winstein S. J. Am. Chem. Soc. 1970, 92: 115

Google Scholar
28 Bagno A. Butts C. Chiappe C. D’Amico F. Lord JCD. Pieraccini D. Rastrelli F. Org. Biomol. Chem. 2005, 3: 1624

Google Scholar
29 Buurma NJ. Pastorello L. Blandamer MJ. Engberts JBFN. J. Am. Chem. Soc. 2001, 123: 11848

Google Scholar