Conclusions
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1.
The intramolecular Khand-Pauson reaction is substantially accelerated when it is carried out on the surface of a Chromatographic adsorbent in the absence of a solvent.
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2.
A method has been developed for the preparation of substituted 3-oxabicyclo[3.3.0]-oct-5-en-7-ones, by cyclization of the dicobalt hexacarbonyl complexes of allyl propargyl ethers.
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3.
A novel cyclization reaction of dicobalt hexacarbonyl complexes has been found, which provides a convenient synthetic route to 4-hydroxymethylcyclopent-2-en-1-ones.
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Literature cited
D. C. Billington and D. Wilson, Tetrahedron Lett.,25, 4041 (1984).
G. S. Mikaélyan and V. A. Smit, Izv. Akad. Nauk SSSR, Ser. Khim., 2652 (1984).
P. L. Pauson, Tetrahedron,41, 5855 (1985).
S. O. Simonian, W. A. Smit, A. S. Gybin, et al., Tetrahedron Lett.,27, 1245 (1986).
L. Paquette, Recent Advances in Polyquinane Chemistry, Topics in Current Chemistry,119, 158 (1984).
R. J. Trautman, D. C. Gross, and P. C. Ford, J. Am. Chem. Soc.,107, 2355 (1985).
G. H. Posner, Angew. Chem.,90, 527 (1978).
A. McKillop and D. W. Young, Synthesis (1979), pp. 401, 481.
G. Rosini, R. Ballini, and P. Sorrenti, Synthesis (1983), p. 1014.
G. Rosini, E. Marotta, R. Ballini, and M. Petrini. Synthesis (1986), p. 237.
F. Texier-Boullet, B. Klein, and J. Hamelin, Synthesis (1986), p. 409.
R. Boothe, C. Dial, R. Conway, et al., Tetrahedron Lett.,27, 2207 (1986).
C. Aronovitch and Y. Mazur, J. Org. Chem.,50, 149 (1985).
R. Farwaha, P. de Mayo, and Y. C. Toong, J. Chem. Soc., Chem. Communs., 739 (1983).
V. B. Kazanskii, Kinet. Katal.,28, 47 (1987).
F. Menger, Acc. Chem. Res., 128 (1985).
R. Nakamura, A. Oomura, N. Okada, and E. Echigoya, Chem. Lett., 1463 (1982).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2802–2812, December, 1988.
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Smit, V.A., Simonyan, S.O., Tarasov, V.A. et al. Intramolecular cyclization of dicobalt hexacarbonyl complexes of allyl propyl ethers on adsorbent surfaces. A convenient mode of preparation of 3-oxabicyclo[3.3.0]octenes and 4-hydroxymethylcyclopentenone derivatives. Russ Chem Bull 37, 2526–2535 (1988). https://doi.org/10.1007/BF00952633
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DOI: https://doi.org/10.1007/BF00952633