Intramolecular Friedel-Crafts acylations of 1- and 2-alkanoic acid diene tricarbonyliron complexes

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8763-8766

  Franck Neumann, Michel ^a   Miesch Gross, Laurence ^a   Nass, Olivier ^a  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IRON COMPLEX;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; SYNTHESIS;

EID: 0030602155     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02044-8     Document Type: Article

References (20)

1. 1. Unfunctionalized diene complexes : Graf, R.E.; Lillya, C.P. J. Organomet. Chem. 1979, 166, 53-62 and ref. therein. Functionalized diene complexes : Franck-Neumann, M.; Sedrati, M.; Mokhi, M. New J. Chem., 1990, 14, 471-480.
2. 1. Unfunctionalized diene complexes : Graf, R.E.; Lillya, C.P. J. Organomet. Chem. 1979, 166, 53-62 and ref. therein. Functionalized diene complexes : Franck-Neumann, M.; Sedrati, M.; Mokhi, M. New J. Chem., 1990, 14, 471-480.
3. 2. Greaves, E.O.; Knox, G.R.; Pauson, P.L.; Toma, S. J.C.S. Chem. Comm. 1974, 257-258 and ref. therein.
4. 3. Franck-Neumann, M.; Sedrati, M.; Abdali, A. J. Organomet. Chem. 1988, 339, C9-C12.
5. 4. This is probably the case for the carbonylative annulation of myrcene tricarbonyliron by reaction with oxalyl chloride (35-40 % mixture of cyclic six-membered diastereomers) : Birch, A.J.; Pearson, A.J. J.C.S. Chem. Comm. 1976, 601-602.
6. 5. Five membered cyclic ketones condensed with conjugated diene units can be valuable intermediates for the synthesis of polyquinanes and related structures. In this context, decomplexation with cyclocarbonylation of adequately substituted diene tricarbonyliron complexes may be useful : Franck-Neumann, M.; Vernier, J.M. Tetrahedron Lett., 1992, 33, 7361-7364 Franck-Neumann, M.; Vernier, J.M. Tetrahedron Lett., 1992, 33, 7365-7368.
7. 5. Five membered cyclic ketones condensed with conjugated diene units can be valuable intermediates for the synthesis of polyquinanes and related structures. In this context, decomplexation with cyclocarbonylation of adequately substituted diene tricarbonyliron complexes may be useful : Franck-Neumann, M.; Vernier, J.M. Tetrahedron Lett., 1992, 33, 7361-7364 Franck-Neumann, M.; Vernier, J.M. Tetrahedron Lett., 1992, 33, 7365-7368.
8. 6. Bertele, E.; Schudel, P. Helv. Chim. Acta, 1967, 50, 2445-2456.
9. 17).
10. 3, 50 MHz, ppm/TMS) : 6 : δ = 20.7, 24.4, 38.0, 48.4, 70.3, 88.0, 107.2, 209.7; 9 : δ = 27.9, 35.5, 39.4, 60.2, 80.5, 120.8, 209.3, 213.8.
11. 3 was however not the solution, since the reaction stopped then far from completion.
12. 10. An almost pure sample of the Z isomer of the acid 2, prepared by Wittig reaction of α-methacroleine with the ylid from (4-carboethoxybutyl) triphenyl phosphonium bromide, gave only poor yields of intramolecular acylation products, the major isomer formed being anew the Z dienone complex 6 (25 % at best, under the favourable influence of a CO atmosphere) !
13. 3, also without a Lewis acid has been described : Nakanishi, S.; Kumeta, K.; Otsuji, Y. Tetrahedron Lett., 1994, 35, 3727-3728.
14. 3 (75 % isomerization Z → E, without reaction).
15. 13. The details of the X-ray structure determination will be given in the full paper. Ortep view 6 :
16. 14. With cerium ammonium nitrate (CAN) in dry acetone the complexes 6 and 7 led respectively to the corresponding relatively unstable Z-dienone (67 % + 19 % SM, 4 h at -50° C) and very stable E-dienone (87 %, 5 min at 25° C). Similarly the complex 9 gave 3-vinyl-2-cyclopentenone (95%).
17. 15. An interesting intramolecular Friedel-Crafts reaction has been described in the cyclobutandiene tricarbonyliron series, leading to 1,2 "ortho" and 1,3"para" (major) cyclizations : Adams, C.M.; Crawford, E.S.; Salim, E. Tetrahedron Lett., 1992, 33, 3963-3966.
18. 16. The Friedel-Crafts reaction of butadiene tricarbonyliron with ω-diacid dichlorides led only to consecutive intermolecular acylations : Sapienza, R.S.; Riley, P.E.; Davis, R.E.; Pettit, R. J. Organometal. Chem., 1976, 121, C35-C40.
19. 17. Corey, E. J.; Boaz, N.W. Tetrahedron Lett., 1985, 26, 6019-6022. Magot-Cuvru, A.; Blanco, L.; Drouin, J. Tetrahedron, 1991, 47, 8331-8338.
20. 17. Corey, E. J.; Boaz, N.W. Tetrahedron Lett., 1985, 26, 6019-6022. Magot-Cuvru, A.; Blanco, L.; Drouin, J. Tetrahedron, 1991, 47, 8331-8338.