Tin-hydride-mediated radical addition of alkyl halides to 2-methylene-1,3-dithiane monoxide as a ketene equivalent

Heterocycles

Volumn 80, Issue 1, 2010, Pages 259-267

  Yoshida, Suguru ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

2 Methylene 1,3 dithiane 1 Oxide; Addition Reaction; Ketene Equivalent; Radical Reaction; Sulfur

Indexed keywords

EID: 76949105920     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-09-S(S)6     Document Type: Article

References (23)

1. Curran D.P. Synthesis (1988) 417
2. Giese B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds (1986), Pergamon Press, Oxford, U.K. Chapter 3
3. Zard S.Z. Radical Reactions in Organic Synthesis (2003), Oxford University Press, Oxford, U.K. Chapter 2
4. Togo H. Advanced Free Radical Reactions for Organic Synthesis (2004), Elsevier, Oxford, U.K. Chapter 4
5. Yoshida S., Yorimitsu H., and Oshima K. J. Organomet. Chem. 692 (2007) 3110
6. Yoshida S., Yorimitsu H., and Oshima K. Org. Lett. 9 (2007) 5573
7. Yoshida S., Yorimitsu H., and Oshima K. Chem. Lett. 37 (2008) 786
8. Yoshida S., Yorimitsu H., and Oshima K. Synlett (2007) 1622
9. Yoshida S., Yorimitsu H., and Oshima K. Heterocycles 76 (2008) 679
10. Viehe H.G., Janousek Z., and Merenyi R. Acc. Chem. Res. 18 (1985) 148
11. A part of this work was communicated: in press. Yoshida S., Yorimitsu H., and Oshima K. Chem. Lett. (2009) 38
12. Radical addition to ketene and its related compounds is rare and difficult to control. Huang W., Henry-Riyad H., and Tidwell T.T. J. Am. Chem. Soc. 121 (1999) 3939
13. Sung K., and Tidwell T.T. J. Org. Chem. 63 (1998) 9690
14. Ogura K., Sumitani N., Kayano A., Iguchi H., and Fujita M. Chem. Lett. (1992) 1487
15. Chatgilialoglu C., and Newcomb M. Adv. Organomet. Chem. 44 (1999) 67
16. The relative stereochemistry of 3 was determined by comparing the NMR spectra of 3 with those of closely related compounds. See:. Page P.C.B., Wilkes R.D., Namwindwa E.S., and Witty M.J. Tetrahedron 52 (1996) 2125
17. Greef M., and Zard S.Z. Tetrahedron 60 (2004) 7781
18. Sliwinska A., and Zwierzak A. Tetrahedron 59 (2003) 5927
19. Seebach D., Grobel B.T., Beck A.K., Braun M., and Geiss K.H. Int. Ed. Engl. 11 (1972) 443
20. Kaya R., and Beller N.R. J. Org. Chem. 46 (1981) 196
21. Sandrinelli F., Fontaine G., Perrio S., and Beslin P. J. Org. Chem. 69 (2004) 6916
22. Ohmiya H., Tsuji T., Yorimitsu H., and Oshima K. Chem. Eur. J. 10 (2004) 5640
23. Sai M., Someya H., Yorimitsu H., and Oshima K. Org. Lett. 10 (2008) 2545