Radical carbonylation of 1,5-enynes using TTMSS as a chain carrier. Unexpected formation of persistent 3-silyl-1-siloxyallyl radicals serving as a chain breaking path

Chemistry Letters

Volumn 33, Issue 7, 2004, Pages 854-855

  Fukuyama, Takahide ^a   Uenoyama, Yoshitaka ^a   Oguri, Shinya ^a   Otsuka, Noboru ^a   Ryu, Ilhyong ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CYCLOPENTANONE DERIVATIVE; OXYGEN; RADICAL; SILANE DERIVATIVE; TRIS(TRIMETHYLSILYL)SILANE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; ISOLATION PROCEDURE; PREDICTION; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 4644349439     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.854     Document Type: Article

References (14)

1. Reviews: a) I. Ryu and N. Sonoda, Angew. Chem., Int. Ed. Engl., 35, 1050 (1996). b) I. Ryu, N. Sonoda, and D. P. Curran, Chem. Rev., 96, 177 (1996). c) I. Ryu, Chem. Soc. Rev., 30, 16 (2001). d) I. Ryu, Chem. Rec., 2, 249 (2002). Also see a review on acyl radicals: e) C. Chatgilialoglu, D. Crich, M. Komatsu, and I. Ryu, Chem. Rev., 99, 1991 (1999).
2. Reviews: a) I. Ryu and N. Sonoda, Angew. Chem., Int. Ed. Engl., 35, 1050 (1996). b) I. Ryu, N. Sonoda, and D. P. Curran, Chem. Rev., 96, 177 (1996). c) I. Ryu, Chem. Soc. Rev., 30, 16 (2001). d) I. Ryu, Chem. Rec., 2, 249 (2002). Also see a review on acyl radicals: e) C. Chatgilialoglu, D. Crich, M. Komatsu, and I. Ryu, Chem. Rev., 99, 1991 (1999).
3. Reviews: a) I. Ryu and N. Sonoda, Angew. Chem., Int. Ed. Engl., 35, 1050 (1996). b) I. Ryu, N. Sonoda, and D. P. Curran, Chem. Rev., 96, 177 (1996). c) I. Ryu, Chem. Soc. Rev., 30, 16 (2001). d) I. Ryu, Chem. Rec., 2, 249 (2002). Also see a review on acyl radicals: e) C. Chatgilialoglu, D. Crich, M. Komatsu, and I. Ryu, Chem. Rev., 99, 1991 (1999).
4. Reviews: a) I. Ryu and N. Sonoda, Angew. Chem., Int. Ed. Engl., 35, 1050 (1996). b) I. Ryu, N. Sonoda, and D. P. Curran, Chem. Rev., 96, 177 (1996). c) I. Ryu, Chem. Soc. Rev., 30, 16 (2001). d) I. Ryu, Chem. Rec., 2, 249 (2002). Also see a review on acyl radicals: e) C. Chatgilialoglu, D. Crich, M. Komatsu, and I. Ryu, Chem. Rev., 99, 1991 (1999).
5. Reviews: a) I. Ryu and N. Sonoda, Angew. Chem., Int. Ed. Engl., 35, 1050 (1996). b) I. Ryu, N. Sonoda, and D. P. Curran, Chem. Rev., 96, 177 (1996). c) I. Ryu, Chem. Soc. Rev., 30, 16 (2001). d) I. Ryu, Chem. Rec., 2, 249 (2002). Also see a review on acyl radicals: e) C. Chatgilialoglu, D. Crich, M. Komatsu, and I. Ryu, Chem. Rev., 99, 1991 (1999).
6. C. Chatgilialoglu, Acc. Chem. Res., 25, 188 (1992).
7. I. Ryu, K. Nagahara, A. Kurihara, M. Komatsu, and N. Sonoda, J. Organomet. Chem., 548, 105 (1997).
8. 3Si) 670.3271, found 670.3274.
9. W=0.157 (1 > 5σ(I)) for 10799 observed reflections.
10. The cyclizative silylcarbonylation of 1,5-azaenynes using TTMSS proceeds with smooth chain propagation, see: M. Tojino, N. Otsuka, T. Fukuyama, H. Matsubara, C. H. Schiesser, H. Kuriyama, H. Miyazato, S. Minakata, M. Komatsu, and I. Ryu, Org. Biomol. Chem., 1, 4262 (2003).
11. a) A. Alberti and C. Chatgilialoglu, Tetrahedron, 46, 3963 (1990).
12. b) M. Ballestri, C. Chatgilialoglu, K. B. Clark, D. Griller, B. Giese, and B. Kopping, J. Org. Chem., 56, 678 (1991).
13. S. Nakatani, J. Yoshida, and S. Isoe, J. Chem. Soc., Chem. Commun., 1992, 880.
14. +) 298.1602, found 298.1603.