Carbon Tetrabromide: An Efficient Catalyst for Regioselective Ring Opening of Epoxides with Alcohols and Water

J. S. Yadav; B. V. S. Reddy; K. Harikishan; Ch. Madan; A. V. Narsaiah

doi:10.1055/s-2005-918422

PAPER

Carbon Tetrabromide: An Efficient Catalyst for Regioselective Ring Opening of Epoxides with Alcohols and Water

J. S. Yadav*, B. V. S. Reddy, K. Harikishan, Ch. Madan, A. V. Narsaiah
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;

Abstract

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Abstract

Epoxides undergo rapid ring opening with a range of alcohols in the presence of catalytic amount of carbon tetrabromide under mild and convenient conditions to afford the corresponding β-alkoxy alcohols and 1,2-diols in high yields with high regioselectivity.

Keywords

epoxides - carbon tetrabromide - alcohols - β-hydroxy ethers

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References

<A NAME="RZ23004SS-1A">1a</A> Parker RE. Isaacs NS. Chem. Rev. 1959, 59: 737

<A NAME="RZ23004SS-1B">1b</A> Bonini C. Righi G. Synthesis 1994, 225

<A NAME="RZ23004SS-1C">1c</A> Paknikar SK. Kirtane JG. Tetrahedron 1983, 39: 2323

<A NAME="RZ23004SS-1D">1d</A> Yadav JS. Reddy BVS. Basak AK. Narsaiah AV. Tetrahedron Lett. 2003, 44: 1047

<A NAME="RZ23004SS-2A">2a</A> Corey EJ. Cheng X.-M. The Logic of Chemical Synthesis Wiley; New York: 1989.

<A NAME="RZ23004SS-2B">2b</A> Kino T. Halanaka H. Hashimoto M. Nishiyama M. Goto T. Okuhara M. Kohsaka M. Aoki H. Imanaka H. J. Antibiot. 1987, 40: 1249

<A NAME="RZ23004SS-3">3</A> Smith JC. Synthesis 1984, 629

<A NAME="RZ23004SS-4A">4a</A> Rosowoslay A. In Heterocyclic Compounds with Three- and Four-Membered Rings Part 1: Weissberger A. Wiley-Interscience; New York: 1964.

<A NAME="RZ23004SS-4B">4b</A> Winston S. Henderson RD. J. Am. Chem. Soc. 1943, 65: 2190

<A NAME="RZ23004SS-5">5</A> Olah GA. Fung AP. Meider D. Synthesis 1981, 280

<A NAME="RZ23004SS-6">6</A> Posner GH. Pogers DZ. Kinzig CH. Gurria GM. Tetrahedron Lett. 1975, 3597

<A NAME="RZ23004SS-7">7</A> Otera J. Yashinaga Y. Hirakawa K. Tetrahedron Lett. 1985, 26: 3219

<A NAME="RZ23004SS-8">8</A> Iranpoor N. Boltork IM. Tetrahedron Lett. 1990, 31: 735

<A NAME="RZ23004SS-9">9</A> Iranpoor N. Boltork IM. Synth. Commun. 1990, 20: 2789

<A NAME="RZ23004SS-10">10</A> Iranpoor N. Salehi P. Synthesis 1994, 1152

<A NAME="RZ23004SS-11">11</A> Chini M. Chrotti P. Gardelli C. Macchia F. Synlett 1992, 673

<A NAME="RZ23004SS-12A">12a</A> Corey EJ. Fuchs PL. Tetrahedron Lett. 1972, 3769

<A NAME="RZ23004SS-12B">12b</A> Lee A.-S.-Y. Su F.-Y. Liao Y.-C. Tetrahedron Lett. 1999, 40: 1323

<A NAME="RZ23004SS-12C">12c</A> Johnstone C. Kerr WJ. Scott JS. Chem. Commun. 1996, 341

<A NAME="RZ23004SS-12D">12d</A> Huh DH. Jeong JS. Lee HB. Ryu H. Kim YG. Tetrahedron 2002, 58: 9925

<A NAME="RZ23004SS-12E">12e</A> Nishida Y. Shingu Y. Dohl H. Kobayashi K. Org. Lett. 2003, 5: 2377

<A NAME="RZ23004SS-13A">13a</A> Yadav JS. Reddy BVS. Basak AK. Narsaiah AV. Tetrahedron Lett. 2003, 44: 2217

<A NAME="RZ23004SS-13B">13b</A> Yadav JS. Reddy BVS. Sadashiv K. Harikishan K. Narsaiah AV. J. Mol. Catal. A. 2004, 220: 153

<A NAME="RZ23004SS-13C">13c</A> Yadav JS. Reddy BVS. Reddy PSR. Basak AK. Narsaiah AV. Adv. Synth. Catal. 2004, 346: 77

<A NAME="RZ23004SS-13D">13d</A> Yadav JS. Reddy BVS. Basak AK. Visali B. Narsaiah AV. Nagaiah K. Eur. J. Org. Chem. 2004, 546

<A NAME="RZ23004SS-14A">14a</A> Chitwood HC. Freure BT. J. Am. Chem. Soc. 1946, 68: 680

<A NAME="RZ23004SS-14B">14b</A> Gagnaire D. Bull. Soc. Chim. Fr. 1960, 1813