Synthesis, Table of Contents PAPER© Georg Thieme Verlag Stuttgart · New YorkSelective Fries Rearrangement Catalyzed by Zinc PowderSatya Paul*, Monika GuptaDepartment of Chemistry, University of Jammu, Jammu-180 006, IndiaFax: +91(191)2505086; e-Mail: paul7@rediffmail.com; Recommend Article Abstract Buy Article All articles of this category Corrected by:Selective Fries Rearrangement Catalyzed by Zinc PowderSynthesis 2004; 2004(12): 2074-2074DOI: 10.1055/s-2004-829198 Abstract Zinc powder in the presence of N,N-dimethylformamide efficiently catalyzes the selective Fries rearrangement of acetylated phenols under microwave heating or with conventional heating using an oil bath. In some cases different products were obtained using microwave heating and conventional heating. Selective migration of the acyl group has been noted with good yields. Keywords acetylated phenols - zinc powder - Fries rearrangement - microwave activation - selectivity Full Text References References and Notes <A NAME="RZ00404SS-1A">1a</A> Olah GA. Friedel-Crafts Chemistry Wiley-Interscience; New York: 1983. <A NAME="RZ00404SS-1B">1b</A> Clark JH. In Catalysis of Organic Reactions by Supported Inorganic Reagents VCH; New York: 1994. Chap 3. p.41 <A NAME="RZ00404SS-2">2</A> Martin R. Org. Prep. Proced. Int. 1992, 24: 369 <A NAME="RZ00404SS-3A">3a</A> Metivier P. In Fine Chemicals through Heterogeneous Catalysis Sheldon RA. Van Bekkum H. Wiley-VCH; Weinheim: 2001. Chap 4. p.161 <A NAME="RZ00404SS-3B">3b</A> Guisnet M. Perot G. In Fine Chemicals through Heterogeneous Catalysis Wiley-VCH; Weinheim: 2001. Chap 5. p.211 <A NAME="RZ00404SS-4">4</A> Motherwell WB. Vazquez S. Tetrahedron Lett. 2000, 41: 9667 ; and references cited therein <A NAME="RZ00404SS-5">5</A> Terunori F, and Masaharn I. inventors; Jpn. Kokai Tokkyo Koho, JP 60252444. ; Chem. Abstr. 1986, 104, 168144q <A NAME="RZ00404SS-6">6</A> Vogt A. Kouwenhovn HW. Prins R. Appl. Catal. A: Gen. 1995, 123: 37 ; and references cited therein <A NAME="RZ00404SS-7">7</A> Heidekum A. Harmer MA. Hoelderich WF. J. Catal. 1998, 176: 260 <A NAME="RZ00404SS-8">8</A> Kobayashi S. Moriwaki M. Hachiya I. Tetrahedron Lett. 1996, 37: 2053 <A NAME="RZ00404SS-9">9</A> Clark JH. Dekamin MG. Moghaddam FM. Green Chem. 2002, 4: 366 <A NAME="RZ00404SS-10">10</A> Harjani JR. Nara SJ. Salunkhe MM. Tetrahedron Lett. 2001, 42: 1979 <A NAME="RZ00404SS-11">11</A> Olah GA. Arvanaghi M. Krishnamurthy VV. J. Org. Chem. 1983, 48: 3359 <A NAME="RZ00404SS-12">12</A> Moghaddam FM. Dakamin MG. Tetrahedron Lett. 2000, 41: 3479 <A NAME="RZ00404SS-13">13</A> Khadilkar BM. Madyar VR. Synth. Commun. 1999, 29: 1195 <A NAME="RZ00404SS-14A">14a</A> Kad GL. Trehan IR. Kaur J. Nayyar S. Arora A. Brar JS. Indian J. Chem., Sect. B 1996, 35: 734 <A NAME="RZ00404SS-14B">14b</A> Trehan IR. Brar JS. Arora AK. Kad GL. J. Chem. Edu. 1997, 74: 324 <A NAME="RZ00404SS-15A">15a</A> Caddick S. Tetrahedron 1995, 57: 10403 <A NAME="RZ00404SS-15B">15b</A> Varma RS. Green Chem. 1999, 1: 43 <A NAME="RZ00404SS-15C">15c</A> Loupy A. Petit A. Hamelin J. Texier-Boullet F. Jacquault P. Mathé D. Synthesis 1998, 1213 <A NAME="RZ00404SS-15D">15d</A> de la Hoz A. Diaz-Ortis A. Moreno A. Langa F. Eur. J. Org. Chem. 2000, 3659 <A NAME="RZ00404SS-15E">15e</A> Lidström P. Tierney J. Wathey B. Westman J. Tetrahedron 2001, 57: 9225 <A NAME="RZ00404SS-15F">15f</A> Microwaves in Organic Synthesis Loupy A. Wiley-VCH; Weinheim Germany: 2002. <A NAME="RZ00404SS-16">16</A> Ishino Y. Mihara M. Takeuchi T. Takemoto M. Tetrahedron Lett. 2004, 45: 3503 <A NAME="RZ00404SS-17">17</A> Amano M. Saiga A. Ikegami R. Ogata T. Takagi K. Tetrahedron Lett. 1998, 39: 8667 <A NAME="RZ00404SS-18">18</A> Ogawa Y. Saiga A. Mori M. Shibata T. Takegi K. J. Org. Chem. 2000, 65: 1031 <A NAME="RZ00404SS-19">19</A> Chavan SP. Shivasankar K. Sivappa R. Kale R. Tetrahedron Lett. 2002, 43: 8583 <A NAME="RZ00404SS-20">20</A> Yadav JS. Reddy BVS. Kondaji G. Rao RS. Kumar SP. Tetrahedron Lett. 2002, 43: 8133 <A NAME="RZ00404SS-21">21</A> Paul S. Nanda P. Gupta R. Loupy A. Synthesis 2003, 2877