New opportunities for α-ketenyl radicals in ring synthesis

Tetrahedron Letters

Volumn 39, Issue 38, 1998, Pages 6971-6974

  De Boeck, Benoît ^a   Herbert, Nicola ^a   Pattenden, Gerald ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; BICYCLO[6.1.0]NONANONE DERIVATIVE; FREE RADICAL; KETENE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERISM; SYNTHESIS;

EID: 0032541682     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01479-8     Document Type: Article

References (17)

1. 1 Hayes, C. J.; Pattenden, G.; Tetrahedron Lett., 1996, 37, 271-274.
2. 2 Herbert, N.; Pattenden, G.; Synlett, 1997, 69-70.
3. 2-sp rehybridisation of the acyl radical centre in 1.
4. 4 a) Grieco, P. A.; Yaw, J. Y.; Claremon, D. A.; Nicolaou, K. C.; J. Org. Chem., 1981, 46, 1215-1217.
5. b) Nicolaou, K. C.; Petasis, N. A.; Claremon, D. A.; Tetrahedron ,1985, 41, 4835-4841.
6. 5 An attempt to cyclise phenyl o-ethynylbenzoselenoate under similar conditions led only to decomposition of the starting material without formation of any identifiable product.
7. 6 All new compounds showed satisfactory spectroscopic data together with mass spectrometry or microanalytical data.
8. 7 Brown, R. F. C.; Butcher, M.; Aust. J. Chem., 1970, 23, 1901-1905.
9. 8 For related o-formyl benzoyl radical cyclisations, see :a) Harrison, D. A.; Schwartz, R. N.; Kagan, J.; J. Am. Chem. Soc., 1970, 92, 5793-5795.;
10. b) Kende, A. S.; Belletire, J. L.; Tetrahedron Lett., 1972, 2145-2148.;
11. c) Praefcke, K.; Tetrahedron Lett., 1973, 973-976.;
12. d) Scaiano, J. C.; Encinas, M. V.; George, M. V.; J. Chem. Soc., Perkin Trans. II, 1980, 724-730.;
13. e) Mendenhall, G. D.; Protasiewicz, J. D.; Brown, C. E.; Ingold, K. U.; Lusztyk, J.; J. Am. Chem. Soc., 1994, 116, 1718-1724.;
14. f) Yamamoto, Y.; Ohno, M.; Eguchi, S.; J. Org. Chem., 1996, 61, 9264-9271.
15. 9 Crich, D.; Yao, Q.; J. Org. Chem., 1996, 61, 3566-3570.
16. 3SnH-AIBN gave similar results although 2-phenylcyclobutanone 33 was also obtained in 37% yield. This compound is probably the result of a 4-exo-dig cyclisation of the intermediate benzylic radical 32 onto the ketene moiety present after opening of the cyclopropane ring. (Equation presented)
17. 11 We thank Dr A. J. Blake at this department for determining this X-ray structure which will be published separately in a full paper.