Chemoselective Thioacetalization Using 3-(1,3-Dithian-2-ylidene)pentane-2,4-dione as an Odorless and Efficient Propane-1,3-dithiol Equivalent under Solvent-Free Conditions

Yan Ouyang; Dewen Dong; Chunbai Zheng; Haifeng Yu; Qun Liu; Zhenqian Fu

doi:10.1055/s-2006-950298

PAPER

Chemoselective Thioacetalization Using 3-(1,3-Dithian-2-ylidene)pentane-2,4-dione as an Odorless and Efficient Propane-1,3-dithiol Equivalent under Solvent-Free Conditions

Yan Ouyang, Dewen Dong*, Chunbai Zheng, Haifeng Yu, Qun Liu*, Zhenqian Fu
Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. of China
Fax: +86(431)5098635; e-Mail: dongdw663@nenu.edu.cn;

Abstract

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Abstract

As a non-thiolic, odorless propane-1,3-dithiol equivalent, 3-(1,3-dithian-2-ylidene)pentane-2,4-dione has been investigated in acid-promoted thioacetalization under solvent-free conditions. A range of selected aldehydes and aliphatic ketones have been converted into the corresponding dithioacetals in high yields. The relatively slow reaction rate of aromatic ketones allowed chemoselective protection of aromatic aldehydes or aliphatic ketones, in contrast to aromatic ketones.

Key words

chemoselectivity - concentrated hydrochloric acid - solvent-free reaction - thioacetalization - α-oxo ketene S,S-acetals

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References

<A NAME="RF07506SS-1">1</A> Tanaka K. Solvent-Free Organic Synthesis Wiley-VCH; Weinheim: 2003.

<A NAME="RF07506SS-2">2</A> Anastas PT. Warner JC. Green Chemistry: Theory and Practice Oxford; London: 1998.

<A NAME="RF07506SS-3A">3a</A> Rothenberg G. Dowine AP. Raston CL. Scott JL. J. Am. Chem. Soc. 2001, 123: 8701

<A NAME="RF07506SS-3B">3b</A> Bolm C. Palazzi C. Francio G. Leitner W. Chem. Commun. 2002, 1588

<A NAME="RF07506SS-3C">3c</A> Clark JH. Green Chem. 1999, 1

<A NAME="RF07506SS-4A">4a</A> Metzger JO. Angew. Chem. Int. Ed. 1998, 37: 2975

<A NAME="RF07506SS-4B">4b</A> Varma RS. Green Chem. 1999, 43

<A NAME="RF07506SS-5A">5a</A> Toda F. Yagi M. Kiyoshige K. J. Chem Soc., Chem. Commun. 1988, 958

<A NAME="RF07506SS-5B">5b</A> Toda F. Tanaka K. Hamai K. J. Chem. Soc., Perkin Trans. 1 1990, 3207

<A NAME="RF07506SS-5C">5c</A> Tanaka K. Toda F. Chem. Rev. 2000, 100: 1025

<A NAME="RF07506SS-5D">5d</A> Cave GWV. Raston CL. Scott JL. Chem. Commun. 2001, 2159

<A NAME="RF07506SS-6A">6a</A> Firouzabadi H. Iranpoor N. Karimi B. Synthesis 1999, 58

<A NAME="RF07506SS-6B">6b</A> Firouzabadi H. Karimi B. Eslami S. Tetrahedron Lett. 1999, 40: 4055

<A NAME="RF07506SS-6C">6c</A> Firouzabadi H. Iranpoor N. Kamal A. Synthesis 2002, 59

<A NAME="RF07506SS-7A">7a</A> Deka N. Sarma JC. Chem. Lett. 2001, 794

<A NAME="RF07506SS-7B">7b</A> Kazahaya K. Tsuji S. Sato T. Synlett 2004, 1640

<A NAME="RF07506SS-7C">7c</A> Aoyama T. Takido T. Kodomari M. Synlett 2004, 2307

<A NAME="RF07506SS-8A">8a</A> Anand RV. Saravanan P. Singh VK. Synlett 1999, 415

<A NAME="RF07506SS-8B">8b</A> Siddhartha G. Jagat CB. Nabin CB. Synlett 2004, 1592

<A NAME="RF07506SS-9A">9a</A> Kocienski PJ. Protecting Groups Thieme; Stuttgart: 1994.

<A NAME="RF07506SS-9B">9b</A> Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: Wiley; New York: 1999.

<A NAME="RF07506SS-10A">10a</A> Corey EJ. Seebach D. J. Org. Chem. 1966, 31: 4097

<A NAME="RF07506SS-10B">10b</A> Seebach D. Angew. Chem. Int. Ed. Engl. 1979, 18: 239

<A NAME="RF07506SS-10C">10c</A> Rychnovsky SD. Chem. Rev. 1995, 95: 2021

<A NAME="RF07506SS-10D">10d</A> Smith AB. Condon SM. McCauley JA. Acc. Chem. Res. 1998, 31: 35

<A NAME="RF07506SS-10E">10e</A> Breit B. Angew. Chem. Int. Ed. 1998, 37: 453

<A NAME="RF07506SS-10F">10f</A> Smith AB. Pitram SM. Gaunt MJ. Kozmin SA. J. Am. Chem. Soc. 2002, 124: 14516

<A NAME="RF07506SS-11A">11a</A> Ku B. Oh DY. Synth. Commun. 1989, 19: 433

<A NAME="RF07506SS-11B">11b</A> Page PCB. Prodger JC. Westwood D. Tetrahedron 1993, 49: 10355

<A NAME="RF07506SS-11C">11c</A> Kumar P. Reddy RS. Singh AP. Pandey B. Synthesis 1993, 67

<A NAME="RF07506SS-11D">11d</A> Anand RV. Saravanan P. Singh VK. Synlett 1999, 415

<A NAME="RF07506SS-11E">11e</A> Tietze LF. Weigand B. Wulff C. Synthesis 2000, 69

<A NAME="RF07506SS-12A">12a</A> Garlaschelli L. Vidari G. Tetrahedron Lett. 1990, 31: 5815

<A NAME="RF07506SS-12B">12b</A> Patney HK. Tetrahedron Lett. 1991, 32: 2259

<A NAME="RF07506SS-12C">12c</A> Saraswathy VG. Sankararaman S. J. Org. Chem. 1994, 59: 4665

<A NAME="RF07506SS-12D">12d</A> Firouzabadi H. Iranpoor N. Hazarkhani H. J. Org. Chem. 2001, 66: 7527

<A NAME="RF07506SS-12E">12e</A> Kamal A. Chouhan G. Tetrahedron Lett. 2002, 43: 1347

<A NAME="RF07506SS-12F">12f</A> Kamal A. Chouhan G. Tetrahedron Lett. 2003, 44: 3337

<A NAME="RF07506SS-13A">13a</A> Node M. Kumar K. Nishide K. Ohsugi S. Miyamoto T. Tetrahedron Lett. 2001, 42: 9207

<A NAME="RF07506SS-13B">13b</A> Nishide K. Miyamoto T. Kumar K. Ohsugi S. Node M. Tetrahedron Lett. 2002, 43: 8569

<A NAME="RF07506SS-13C">13c</A> Nishide K. Ohsugi S. Fudesaka M. Kodama S. Node M. Tetrahedron Lett. 2002, 43: 5177

<A NAME="RF07506SS-13D">13d</A> Miyazaki T. Han-ya Y. Tokuyama H. Fukuyama T. Synlett 2004, 477

<A NAME="RF07506SS-14A">14a</A> Bertini V. Lucchesini F. Pocci M. De Munno A. Tetrahedron Lett. 1998, 39: 9263

<A NAME="RF07506SS-14B">14b</A> Bertini V. Lucchesini F. Pocci M. De Munno A. J. Org. Chem. 2000, 65: 4839

<A NAME="RF07506SS-14C">14c</A> Bertini V. Pocci M. Lucchesini F. Alfei S. De Munno A. Synlett 2003, 864

<A NAME="RF07506SS-15A">15a</A> Liu Q. Che G. Yu H. Liu Y. Zhang J. Zhang Q. Dong D. J. Org. Chem. 2003, 68: 9148

<A NAME="RF07506SS-15B">15b</A> Yu H. Liu Q. Yin Y. Fang Q. Zhang J. Dong D. Synlett 2004, 999

<A NAME="RF07506SS-15C">15c</A> Dong D. Ouyang Y. Yu H. Liu Q. Liu J. Wang M. Zhu J. J. Org. Chem. 2005, 70: 4535

<A NAME="RF07506SS-16A">16a</A> Yu H. Dong D. Ouyang Y. Liu Q. Wang Y. Lett. Org. Chem. 2005, 2: 755

<A NAME="RF07506SS-16B">16b</A> Dong D. Yu H. Ouyang Y. Liu Q. Bi X. Lu Y. Synlett 2006, 283