Reaction of benzyne with styrene oxide: Insertion of arynes into a C-O bond of epoxides

Synlett

Volumn , Issue 8, 2007, Pages 1308-1310

  Beltrán Rodil, Sandra ^a,b   Peña, Diego ^a   Guitián, Enrique ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Arynes; Epoxides; Furans; Insertions; Ring expansion

Indexed keywords

ARYNE; BENZYNE; CHEMICAL COMPOUND; DIHYDROBENZOFURAN DERIVATIVE; EPOXIDE; STYRENE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION;

EID: 34249780376     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-977460     Document Type: Article

References (16)

1. (a) Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211.
2. (b) Peña, D.; Cobas, A.; Pérez, D.; Guitián, E. Synthesis 2002, 1454.
3. For some recent representative examples, see: (a) Yoshida, H.; Tanino, K.; Ohshita, J.; Kunai, A. Angew. Chem. Int. Ed. 2004, 43, 5052.
4. (b) Tambar, U. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 5340.
5. (c) Liu, Z.; Larock, R. C. J. Am. Chem. Soc. 2005, 127, 13112.
6. (d) Lin, W.; Sapountzis, I.; Knochel, P. Angew. Chem. Int. Ed. 2005, 44, 4258.
7. For a recent highlight, see: Peña, D.; Pérez, D.; Guitián, E. Angew. Chem. Int. Ed. 2006, 45, 3579.
8. Stiles, M.; Burckhardt, U.; Haag, A. J. Org. Chem. 1962, 27, 4715.
9. Recently Yoshida et al. reported the insertion of arynes into the C=O double bond of aldehydes: Yoshida, H.; Watanabe, M.; Fukushima, H.; Ohshita, J.; Kunai, A. Org. Lett. 2004, 6, 4049.
10. Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967.
11. Stiles, M.; Haag, A. personal communication in reference 7 (page 178).
12. 2), 48.5 (CH); MS (EI): m/z (%): 196 (100). GC/MS were performed on an Agilent 6890N/5973 inert instrument with a HP-5MS capillary column (25 mm x 30 m x 25 μm; 70 to 300°C, 30°C/min).
13. Arnold, D. R.; Fahie, B. J.; Lamont, L. J.; Wierzchowski, J.; Young, K. M. Can. J. Chem. 1987, 65, 2734.
14. This mechanism is the same as that proposed in reference 8.
15. The use of other epoxides such us cyclohexene oxide or propylene oxide did not afford the corresponding insertion products.
16. There is only one example of the insertion of arynes into element-element sigma bonds of cyclic molecules, in particular five- and six-membered-ring disilanes, see: Yoshida, H.; Ikadai, J.; Shudo, M.; Ohshita, J.; Kunai, A. Organometallics 2005, 24, 156.