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

All articles of this category

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

Full Text

References

1 Tanaka K. Solvent-Free Organic Synthesis Wiley-VCH; Weinheim: 2003.

2 Anastas PT. Warner JC. Green Chemistry: Theory and Practice Oxford; London: 1998.

3a Rothenberg G. Dowine AP. Raston CL. Scott JL. J. Am. Chem. Soc. 2001, 123: 8701

3b Bolm C. Palazzi C. Francio G. Leitner W. Chem. Commun. 2002, 1588

3c Clark JH. Green Chem. 1999, 1

4a Metzger JO. Angew. Chem. Int. Ed. 1998, 37: 2975

4b Varma RS. Green Chem. 1999, 43

5a Toda F. Yagi M. Kiyoshige K. J. Chem Soc., Chem. Commun. 1988, 958

5b Toda F. Tanaka K. Hamai K. J. Chem. Soc., Perkin Trans. 1 1990, 3207

5c Tanaka K. Toda F. Chem. Rev. 2000, 100: 1025

5d Cave GWV. Raston CL. Scott JL. Chem. Commun. 2001, 2159

6a Firouzabadi H. Iranpoor N. Karimi B. Synthesis 1999, 58

6b Firouzabadi H. Karimi B. Eslami S. Tetrahedron Lett. 1999, 40: 4055

6c Firouzabadi H. Iranpoor N. Kamal A. Synthesis 2002, 59

7a Deka N. Sarma JC. Chem. Lett. 2001, 794

7b Kazahaya K. Tsuji S. Sato T. Synlett 2004, 1640

7c Aoyama T. Takido T. Kodomari M. Synlett 2004, 2307

8a Anand RV. Saravanan P. Singh VK. Synlett 1999, 415

8b Siddhartha G. Jagat CB. Nabin CB. Synlett 2004, 1592

9a Kocienski PJ. Protecting Groups Thieme; Stuttgart: 1994.

9b Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: Wiley; New York: 1999.

10a Corey EJ. Seebach D. J. Org. Chem. 1966, 31: 4097

10b Seebach D. Angew. Chem. Int. Ed. Engl. 1979, 18: 239

10c Rychnovsky SD. Chem. Rev. 1995, 95: 2021

10d Smith AB. Condon SM. McCauley JA. Acc. Chem. Res. 1998, 31: 35

10e Breit B. Angew. Chem. Int. Ed. 1998, 37: 453

10f Smith AB. Pitram SM. Gaunt MJ. Kozmin SA. J. Am. Chem. Soc. 2002, 124: 14516

11a Ku B. Oh DY. Synth. Commun. 1989, 19: 433

11b Page PCB. Prodger JC. Westwood D. Tetrahedron 1993, 49: 10355

11c Kumar P. Reddy RS. Singh AP. Pandey B. Synthesis 1993, 67

11d Anand RV. Saravanan P. Singh VK. Synlett 1999, 415

11e Tietze LF. Weigand B. Wulff C. Synthesis 2000, 69

12a Garlaschelli L. Vidari G. Tetrahedron Lett. 1990, 31: 5815

12b Patney HK. Tetrahedron Lett. 1991, 32: 2259

12c Saraswathy VG. Sankararaman S. J. Org. Chem. 1994, 59: 4665

12d Firouzabadi H. Iranpoor N. Hazarkhani H. J. Org. Chem. 2001, 66: 7527

12e Kamal A. Chouhan G. Tetrahedron Lett. 2002, 43: 1347

12f Kamal A. Chouhan G. Tetrahedron Lett. 2003, 44: 3337

13a Node M. Kumar K. Nishide K. Ohsugi S. Miyamoto T. Tetrahedron Lett. 2001, 42: 9207

13b Nishide K. Miyamoto T. Kumar K. Ohsugi S. Node M. Tetrahedron Lett. 2002, 43: 8569

13c Nishide K. Ohsugi S. Fudesaka M. Kodama S. Node M. Tetrahedron Lett. 2002, 43: 5177

13d Miyazaki T. Han-ya Y. Tokuyama H. Fukuyama T. Synlett 2004, 477

14a Bertini V. Lucchesini F. Pocci M. De Munno A. Tetrahedron Lett. 1998, 39: 9263

14b Bertini V. Lucchesini F. Pocci M. De Munno A. J. Org. Chem. 2000, 65: 4839

14c Bertini V. Pocci M. Lucchesini F. Alfei S. De Munno A. Synlett 2003, 864

15a Liu Q. Che G. Yu H. Liu Y. Zhang J. Zhang Q. Dong D. J. Org. Chem. 2003, 68: 9148

15b Yu H. Liu Q. Yin Y. Fang Q. Zhang J. Dong D. Synlett 2004, 999

15c Dong D. Ouyang Y. Yu H. Liu Q. Liu J. Wang M. Zhu J. J. Org. Chem. 2005, 70: 4535

16a Yu H. Dong D. Ouyang Y. Liu Q. Wang Y. Lett. Org. Chem. 2005, 2: 755

16b Dong D. Yu H. Ouyang Y. Liu Q. Bi X. Lu Y. Synlett 2006, 283