A comparison of hydrogen bonding solvent effects on the singlet oxygen reactions of allyl and vinyl sulfides, sulfoxides, and sulfones

Tetrahedron

Volumn 62, Issue 46, 2006, Pages 10683-10687

  Stensaas, Kristina L ^a   McCarty, Brent V ^a   Touchette, Natacha M ^a   Brock, James B ^a  

^a MILLSAPS COLLEGE   (United States)

Author keywords

Ene reactions; Hydrogen bonding; Singlet oxygen; Sulfides; Sulfones; Sulfoxides

Indexed keywords

ACETONITRILE; ALLYL SULFIDE; BENZENE; CHLOROFORM; METHANOL; SINGLET OXYGEN; SULFONE DERIVATIVE; SULFOXIDE; VINYL DERIVATIVE; WATER;

ARTICLE; CYCLOADDITION; HYDROGEN BOND; PHOTOOXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 33749250046     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.08.084     Document Type: Article

References (16)

1. Stensaas K., Bajaj A., and Al-Turk A. Tetrahedron Lett. 46 (2005) 715-718
2. Stensaas K., Payne J., Ivancic A., Bajaj A., and Al-Turk A. Tetrahedron Lett. 43 (2002) 25-27
3. Stratakis M., and Orfanopoulos M. Tetrahedron 56 (2000) 1595-1615
4. Adam W., Kumar A., and Saha-Moller C. Tetrahedron Lett. 36 (1995) 7853-7854
5. Clennan E., and Chen X. J. Org. Chem. 53 (1988) 3124-3125
6. Clennan E., and Chen X. J. Am. Chem. Soc. 111 (1989) 8212-8218
7. Ando W., Watanabe K., Suzuki J., and Migita T. J. Am. Chem. Soc. 96 (1974) 6766-6768
8. Recent computational studies conducted by Singleton and Houk suggest that the ene reaction may proceed through a two-step no intermediate process involving a transition state with the symmetry of a perepoxide rather than a discrete perepoxide intermediate. Singleton D.A., Hang C., Szymanski M.J., Meyer M.P., Leach A.G., Kuwata K.T., Chen J.S., Greer A., Foote C.S., and Houk K.N. J. Am. Chem. Soc. 125 (2003) 1319-1328
9. Orfanopoulos M., and Foote C. Tetrahedron Lett. (1985) 5991-5994
10. Adam W., and Richter M. Tetrahedron Lett. 34 (1993) 8423-8426
11. Frimer A., Bartlett P., Boschung A., and Jewett J. J. Am. Chem. Soc. 99 (1977) 7977-7986
12. Clennan reported that at <10% conversion, only 68% ene reaction occurs and 32% sulfur oxidation occurs. Sulfur oxidation becomes unimportant at temperatures above -29 °C. See Ref. 6.
13. Akasaka T., Misawa Y., Goto M., and Ando W. Tetrahedron 45 (1989) 6657-6666 This reference reported the same result as ours at 15 °C
14. Clennan E., and Chen X. J. Am. Chem. Soc. 111 (1989) 5787-5792
15. Parham W., and Edwards L. J. Org. Chem. 33 (1968) 4150-4154
16. In: Lide D.R. (Ed). CRC Handbook of Chemistry and Physics. 81st ed. (2000), Chemical Rubber, Boca Raton, FL