A versatile new synthesis of pyrethroid acids

Synthesis (Germany)

Volumn 1983, Issue 12, 1983, Pages 1002-1005

  Brady, William T ^a   Norton, Scott J ^a   Ko, Jinren ^a  

^a UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84990155405     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1983-30600     Document Type: Article

References (18)

1. M. Elliott, N. F. Jones, Chem. Soc. Rev. 7, 473 (1978).
2. W. T. Brady, D. A. Bak, J. Org. Chem. 44, 107 (1979).
3. Dichloroketene is used in the cycloaddition step rather than chlo-roketene because the former gives much better yields of the corresponding cyclobutanones.
4. L. R. Krepski, A. Hassner, J. Org. Chem. 43, 2879 (1978).
5. It is necessary to reductively remove one chlorine atom prior to the ring contraction step because the a, a-dichlorocyclobutanone will undergo a ring-opening reaction upon treatment with base.
6. W. T. Brady, E. F. Hoff, J. Am. Chem. Soc. 91, 5679 (1969).
7. H. E. Zimmerman, A. Mais, J. Am. Chem. Soc. 81, 3644 (1959).
8. J. M. Conia, J. L. Pipoll, Bull. Soc. Chim. Fr. 1963, 1773.
9. J. Salaun, J. M. Conia, Bull. Soc. Chim. Fr. 1968, 3735.
10. J. M. Conia, J. R. Salaun, Acc. Chem. Res. 5, 33 (1972).
11. Y. Inoue, Y. Katauda, A. Nishimura, K. Kitagawa, M. Ohno, Botynu Kagaku 16, 111 (1951); as seen in C. A. 46, 3961 (1952).
12. M. Julia, M. Guy-Rouault, Bull. Soc. Chim. Fr. 1967, 1411.
13. J. Martel, C. Huynh, Bull. Soc. Chim. Fr. 1967, 985.
14. T. Aratani, Y. Yoneyoshi, T. Nagase, Tetrahedron Lett. 1975, 1707.
15. P. Martin, H. Greuter, D. Bellus, J. Am. Chem. Soc. 101, 5853 (1979).
16. M. J. Brink, H. Austermuhle, P. A. Kramer, U. S. Patent 4028418 (1974), Shell; C. A. 85, 20680 (1976).
17. A. F. Bramwell, L. Crombie, P. Hemesley, G. Pattendeu, M. Elliott, N. R Jones, Tetrahedron 25, 1727 (1969).
18. T. Asao, T. Machiguchi, T. Kitamura, Y. Kitahara, J. Chem. Soc. Chem. Commun. 1970. 89.