Addition of CFCl3 to Aromatic Aldehydes under Ultrasonic Irradiation

Balaka Barkakaty; Yutaka Takaguchi; Sadao Tsuboi

doi:10.1055/s-2006-926367

PAPER

Addition of CFCl₃ to Aromatic Aldehydes under Ultrasonic Irradiation

Balaka Barkakaty, Yutaka Takaguchi, Sadao Tsuboi*
Department of Material and Energy Science, The Graduate School of Environmental Science, Okayama University, Tsushima, Okayama 700-8530, Japan
Fax: +81(86)2518898; e-Mail: stsuboi6@cc.okayama-u.ac.jp;

Abstract

All articles of this category

Abstract

Reductive addition of CFCl₃ to aromatic aldehydes under the influence of activated aluminum powder and ultrasonic irradiation produced chlorofluoro carbinols in reasonable to excellent yields.

Key words

chlorofluoro alcohols - aluminum - ultrasonic effects

Full Text

References

<A NAME="RF14205SS-1A">1a</A> Seiler N. Jung MJ. Koch-Weser J. Enzyme-Activated Irreversible Inhibitors Elsevier/North-Holland Biomedical Press; Amsterdam: 1978.

<A NAME="RF14205SS-1B">1b</A> Rando RR. Pharmacol. Rev. 1984, 36: 111

<A NAME="RF14205SS-1C">1c</A> Banks RE. Organofluorine Chemicals and their Industrial Applications Vol. 123: Royal Society of Chemistry; London: 1979. p.154

<A NAME="RF14205SS-1D">1d</A> Banks RE. Organofluorine Chemicals and their Industrial Applications Vol. 123: Royal Society of Chemistry; London: 1979. p.169

<A NAME="RF14205SS-1E">1e</A> Fuller R. Kobayashi Y. Biomedical Aspects of Fluorine Chemistry Kodansha/Elsevier; New York: 1982.

<A NAME="RF14205SS-2A">2a</A> Shimakoshi H. Maeyema Y. Kaieda T. Matsuo T. Matsui E. Naruta Y. Hisaeda Y. Bull. Chem. Soc. Jpn. 2005, 78: 859

<A NAME="RF14205SS-2B">2b</A> Krahl T. Kemintz E. Angew. Chem. Int. Ed. 2004, 43: 6653

<A NAME="RF14205SS-2C">2c</A> Nenajdenko VG. Shastin AV. Korotchenko VN. Varseev GN. Balenkova ES. Eur. J. Org. Chem. 2003, 302

<A NAME="RF14205SS-2D">2d</A> Saikia AK. Tsuboi S. J. Org. Chem. 2001, 66: 643

<A NAME="RF14205SS-3">3</A> Zeifman YV. Postovoi SA. J. Fluorine Chem. 2004, 125: 1815

<A NAME="RF14205SS-4A">4a</A> Boswell GA. Ripka WC. Org. React. (N.Y.) 1974, 21: 1

<A NAME="RF14205SS-4B">4b</A> Sheppard WA. Sharts CM. In Organic Fluorine Chemistry Benjamin, Inc.; New York: 1969. p.185

<A NAME="RF14205SS-4C">4c</A> Haszeldine RN. J. Chem. Soc. 1950, 3037

<A NAME="RF14205SS-4D">4d</A> Leedham K. Haszeldine RN. J. Chem. Soc. 1954, 1634

<A NAME="RF14205SS-4E">4e</A> Culler WR. Waldmen MC. Can. J. Chem. 1969, 47: 3039

<A NAME="RF14205SS-4F">4f</A> Coe PL. Milner NE. J. Organomet. Chem. 1974, 70: 147

<A NAME="RF14205SS-4G">4g</A> Cantacuzene D. Wakselman C. Dorme R. J. Chem. Soc., Perkin Trans. 1 1977, 1365

<A NAME="RF14205SS-4H">4h</A> Umemoto T. Kuriu Y. Nakayama S. Miyano O. Tetrahedron Lett. 1982, 23: 1471

<A NAME="RF14205SS-4I">4i</A> McLoughlin VCR. Throwers J. Tetrahedron 1969, 25: 5921

<A NAME="RF14205SS-4J">4j</A> Kobayashi Y. Kumadaki I. Tetrahedron Lett. 1969, 4095

<A NAME="RF14205SS-4K">4k</A> Ishikawa N. Ochiai M. Nippon Kagaku Kaishi 1973, 2351

<A NAME="RF14205SS-4L">4l</A> Umemoto T. Kuriu Y. Nakayama S. Tetrahedron Lett. 1982, 23: 1169

<A NAME="RF14205SS-4M">4m</A> Umemoto T. Kuriu Y. Miyano O. Tetrahedron Lett. 1982, 23: 3579

<A NAME="RF14205SS-5A">5a</A> Kitazume T. Ishikawa N. J. Am. Chem. Soc. 1985, 107: 5186

<A NAME="RF14205SS-5B">5b</A> Kitazume T. Ishikawa N. Chem. Lett. 1981, 1679

<A NAME="RF14205SS-5C">5c</A> Kitazume T. Ishikawa N. Chem. Lett. 1982, 137: 1453

<A NAME="RF14205SS-5D">5d</A> Kitazume T. Ishikawa N. Nippon Kagaku Kaishi 1984, 1725

<A NAME="RF14205SS-5E">5e</A> Ishikawa N. Takahashi M. Sato T. Kitazume T. J. Fluorine Chem. 1983, 22: 585

<A NAME="RF14205SS-6">6</A> Tanaka H. Yamashita S. Yamanoue M. Torii S. J. Org. Chem. 1989, 54: 444

<A NAME="RF14205SS-7">7</A> Postovoi SA. Kagramanova EM. Mysov EI. Zeifman YV. Russ. Chem. Bull. 1996, 45: 1425

<A NAME="RF14205SS-8">8</A> Hu C.-M. Tu M.-H. J. Fluorine Chem. 1994, 67: 9

<A NAME="RF14205SS-9">9</A> Mason TJ. Chem. Soc. Rev. 1997, 26: 443

<A NAME="RF14205SS-10">10</A> De Souza-Barboza JC. Petrier C. Luche J.-L. J. Org. Chem. 1988, 53: 1212