Anodic olefin coupling reactions involving ketene dithioacetals: Evidence for a 'radical-type' cyclization

Tetrahedron Letters

Volumn 43, Issue 40, 2002, Pages 7159-7161

  Sun, Yongmao ^a   Moeller, Kevin D ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; ALKENE; KETENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037201148     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01663-5     Document Type: Article

References (14)

1. . For a review see: Moeller K.D. Tetrahedron. 56:2000;9527.
2. Reddy S.H.K., Chiba K., Sun Y., Moeller K.D. Tetrahedron. 57:2001;5183.
3. . For additional examples, see: Sun Y., Liu B., Kao J., d'Avignon D.A., Moeller K.D. Org. Lett. 3:2001;1729.
4. RVC=reticulated vitreous carbon (100 PPI from the Electrosynthesis Co, Inc.). Preparative electrolyses were conducted utilizing a Model 630 coulometer, a Model 410 potentiostatic controller, and a Model 420A power supply purchased from The Electrosynthesis Co., Inc.
5. For anodic olefin coupling reactions that lead to 'radical-like' cyclizations involving enol ether radical cation reactions see: Hudson C.M., Moeller K.D. J. Am. Chem. Soc. 116:1994;3347.
6. For detailed mechanistic studies involving enol ether radical cations, see: (a) Horner, J. H.; Taxil, E.; Newcomb, M. J. Am. Chem. Soc. 1992, 124, 5402; (b) Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 2001, 123, 4364; (c) Newcomb, M.; Miranda, N.; Sannigrahi, M.; Huang, X.; Crich, D. J. Am. Chem. Soc. 2001, 123, 6445.
7. For detailed mechanistic studies involving enol ether radical cations, see: (a) Horner, J. H.; Taxil, E.; Newcomb, M. J. Am. Chem. Soc. 1992, 124, 5402; (b) Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 2001, 123, 4364; (c) Newcomb, M.; Miranda, N.; Sannigrahi, M.; Huang, X.; Crich, D. J. Am. Chem. Soc. 2001, 123, 6445.
8. For detailed mechanistic studies involving enol ether radical cations, see: (a) Horner, J. H.; Taxil, E.; Newcomb, M. J. Am. Chem. Soc. 1992, 124, 5402; (b) Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 2001, 123, 4364; (c) Newcomb, M.; Miranda, N.; Sannigrahi, M.; Huang, X.; Crich, D. J. Am. Chem. Soc. 2001, 123, 6445.
9. Beckwith A.L.J., Easton C.J., Serelis A.K. J. Chem. Soc., Chem. Commun. 1980;482.
10. Beckwith A.L.J., Lawrence T., Serelis A.K. J. Chem. Soc., Chem. Commun. 1980;484.
11. Iorga B., Mouriès V., Savignac P. Bull. Soc. Chim. Fr. 134:1997;891.
12. For examples using enol ethers, see: (a) Sutterer, A.; Moeller, K. D. J. Am. Chem. Soc. 2000, 122, 5636; (b) Duan, S.; Moeller, K. D. Org. Lett. 2001, 3, 2685. For examples using ketene dithioacetals, see Ref. 3 in addition to (c) Liu, B.; Moeller, K. D. Tetrahedron Lett. 2001, 42, 7163.
13. For examples using enol ethers, see: (a) Sutterer, A.; Moeller, K. D. J. Am. Chem. Soc. 2000, 122, 5636; (b) Duan, S.; Moeller, K. D. Org. Lett. 2001, 3, 2685. For examples using ketene dithioacetals, see Ref. 3 in addition to (c) Liu, B.; Moeller, K. D. Tetrahedron Lett. 2001, 42, 7163.
14. For examples using enol ethers, see: (a) Sutterer, A.; Moeller, K. D. J. Am. Chem. Soc. 2000, 122, 5636; (b) Duan, S.; Moeller, K. D. Org. Lett. 2001, 3, 2685. For examples using ketene dithioacetals, see Ref. 3 in addition to (c) Liu, B.; Moeller, K. D. Tetrahedron Lett. 2001, 42, 7163.