Abstract
By reaction of excess benzaldehyde with cyclohexene in presence of sulfuric acid besider-2,c-4-diphenyl-(t-4aH,c-8aH)-hexahydro-4H-1,3-benzodioxin (2) andr-4-phenyl-(t-4aH,c-8aH)-hexahydro-4H-1,3,2-benzodioxathiin-2,2-dioxide (3),trans-2-benzyloxycyclohexyl phenyl ketone (5) and (E)-3-benzylidene-1-cyclohexenyl phenyl ketone (6) are obtained. The formation of5 and6 is shown to proceed via an acid catalyzedCannizzaro reaction of benzaldehyde.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literatur
E. Arundale undL. A. Mikeska, Chem. Rev.51, 505 (1952);
C. W. Roberts, in: Friedel-Crafts and Related Reactions, Vol. 2, S. 1175 (G. A. Olah, Hrsg.). New York: Interscience. 1964
V. I. Isagulyants, T. G. Khaimova, V. R. Melikyan undS. V. Pokrovskaya, Russ. Chem. Rev.37, 17 (1968).
H. Griengl undK. P. Geppert, Mh. Chem.107, 421 (1976).
P. Nowak, Dissertation, Technische Hochschule in Graz, 1973;H. Griengl undP. Nowak, in Vorbereitung.
R. E. Christ undR. C. Fuson, J. Amer. Chem. Soc.59, 893 (1937).
E. M. Arnett, in: Progr. Phys. Org. Chem., Vol.1, S. 296 (S. G. Cohen, A. Streitwieser, Jr., undR. W. Taft, Hrsg.), New York: Interscience. 1963.
E. M. Arnett, R. P. Quirk undJ. W. Larsen, J. Amer. Chem. Soc.92, 3977 (1970).
T. A. Geissman, Org. Reactions2, 94 (1944).
J. F. Walker, Formaldehyde, 3. Aufl., S. 214. New York: Reinhold. 1964
, Formaldehyde, 3. Aufl., S. 253.
C. D. Nenitzescu, in: Carbonium Ions, Vol. 2, S. 510 (G. A. Olah undP. v. R. Schleyer, Hrsg.). New York: Wiley. 1970.
L. M. Pugach, N. D. Gil'chenok, G. S. Idlis undS. K. Ogorodnikov, Zh. Org. Khim.10, 925 (1974) [Chem. Abstr.81, 49048 (1974)].
N. C. Deno, H. J. Peterson undG. S. Saines, Chem. Rev.60, 7 (1960).
J. L. Franklin, in: Carbonium Ions, Vol. 1, S. 93 (G. A. Olah undP. v. R. Schleyer, Hrsg.). New York: Wiley. 1968.
R. L. Shriner undA. Berger, J. Org. Chem.6, 305 (1941).
H. Hosoya undS. Nagakura, Bull. Chem. Soc. Japan37, 1500 (1964).
F. Carré undR. Corriu, Bull. Soc. Chim. France1967, 2898.
J. Roček, Tetrahedron Letters1959, Nr. 5,1;J. Roček undC.-S. Ng, J. Org. Chem.38, 3348 (1973).
F. R. Duke, Anal. Chem.19, 661 (1947).
A. T. Blomquist undJ. Wolinsky, J. Amer. Chem. Soc.79, 6025 (1957).
R. A. Cox, J. Amer. Chem. Soc.96, 1059 (1974).
D. D. Traficante undG. E. Maciel, J. Phys. Chem.70, 1314 (1966).
S. Olsen, Z. Naturforsch.1, 676 (1946);J. W. Baker, J. Chem. Soc.1948, 89;J. W. Baker, J. Chem. Soc.1949, 770;H. J. Prins, Rec. Trav. Chim. Pays-Bas71, 1131 (1952).
Author information
Authors and Affiliations
Additional information
2. Mitt.:H. Griengl undK. P. Geppert, Mh. Chem.107, 675 (1976).
Rights and permissions
About this article
Cite this article
Griengl, H., Nowak, P. Prins-Reaktionen mit Arylaldehyden, 3. Mitt.. Monatshefte für Chemie 108, 407–416 (1977). https://doi.org/10.1007/BF00901994
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00901994