Synthesis of vicinal bis(alkylthio) derivatives by reductive coupling of dithioacetals derived from aromatic aldehydes with low valent titanium iodide species

Chemistry Letters

Volumn , Issue 7, 2001, Pages 640-641

  Yoshimura, Naritoshi ^a   Igarashi, Koji ^a   Funasaka, Setsuo ^a   Mukaiyama, Teruaki ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035614248     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.640     Document Type: Article

References (18)

1. For reviews, see: a) G. M. Robertson, in "Comprehensive Organic Synthesis," ed. by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 3, p. 563.
2. b) T. Wirth, Angew. Chem., Int. Ed. Engl. 35, 61 (1996).
3. c) A. Fürstner and B Bogdanovic, Angew. Chem., Int. Ed. Engl., 35, 2442 (1996).
4. a) T. Mukaiyama, N. Yoshimura, and K. Igarashi, Chem. Lett., 2000, 838.
5. b) T. Mukaiyama, N. Yoshimura, K. Igarashi, and A. Kagayama, Tetrahedron, 57, 2499 (2001). Recent reports of pinacol coupling reaction by using titanium iodide species, see:
6. c) S. Talukdar, S. K. Nayak, and A. Banerji, J. Org. Chem., 63, 4925 (1998).
7. d) R. Hayakawa and M. Shimizu, Chem. Lett., 2000, 724.
8. H. Ishikawa and T. Mukaiyama, Bull. Chem. Soc. Jpn., 51, 2059 (1978).
9. T. W. Greene and P. G. M. Wuts, in "Protective Groups in Organic Synthesis, Third Edition," John Wiley & Sons, New York (1999), p. 293.
10. For reviews, see: a) T. Takeda and T. Fujiwara, Yuki Gosei Kagaku Kyokaishi, 56, 1048 (1998).
11. b) T. Takeda, M. A. Rahim, M. Takamori, K. Yanai, and T. Fujiwara, Polyhedron, 19, 593 (2000). And recent reports were as follows:
12. c) T. Takeda, N. Saeki, Y. Takagi, and T. Fujiwara, Chem. Lett., 2000, 1198.
13. d) T. Fujiwara, K. Yanai, K. Shimane, M. Takamori, and T. Takeda, Eur. J. Org. Chem., 2001, 155.
14. A preparative method of vicinal bis(alkylthio) derivatives was reported by diisopropylamide-induced fragmentation of dibenzyl disulfide, followed by trapping with alkyl halides, see: a) H. Ikehara and S. Tanimoto, Bull. Chem. Soc. Jpn., 57, 1423 (1984).
15. b) S. Tanimoto, S. Nozawa, and Y. Inoue, Bull. Inst. Chem. Res., Kyoto Univ., 68, 193 (1990).
16. 2O and ether, then dried under vacuum at 100 °C. Manganese was dried under vacuum at 100 °C.
17. 4. After filtration and concentration, the crude product was purified by thin layer chromatography to afford the desired vicinal bis(alkylthio) derivative (0.043 g, 95% yield).
18. When titanium(IV) bromide and titanium(IV) chloride were employed in place of titanium(IV) iodide using double molar amounts of the respective initial and additional zinc, the yields of vicinal bis(alkylthio) derivative a little decreased (82% [dl / meso = 49 / 51] and 92% [dl / meso = 50 / 50], respectively). On the other hand, when the procedure of ref 3 was applied, the reaction did not proceed at all.