Abstract
As early as 1909 Paternò and Chieffi [1] had noticed that trimethylene oxides (oxetane, 1) were formed by the photochemical addition of aldehydes or ketones to olefins. At that time, this work did not find the attention it deserved. The present interest in the reaction discovered by Paternò, and in the reaction mechanism stems from the work of Büchi et al. [2], and the reaction is therefore known (cf. Yang [3]) as the Paternò-Büchi reaction. A general survey on preparation and properties of oxetanes will be found elsewhere [4].
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
E. Paternò and G. Chieffi: Gazz. Chim. Ital. 39, I, 341 (1909).
G. Büchi, C. G. Inman and E. S. Lipinsky: J. Amer. chem. Soc. 76, 4327 (1954).
N. C. Yang: Pure Appl. Chem. 9, 591 (1964).
S. Searles Jr. in: Heterocyclic compounds with three- and four-membered rings, ed. by A. Weissberger, Part. 2, pp. 983–1068; esp. p. 990, 1045 (The Chemistry of Heterocyclic Compounds, Vol. 19). New York: Interscience 1964.
N. C. Yang, M. Nussim, M. J. Jorgenson and S. Murov: Tetrahedron Letters 1964, 3657.
J. D. Margerum, J. N. Pitts Jr., J. G. Rutgers and S. Searles: J. Amer. chem. Soc. 81, 1549 (1959).
L. A. Singer and P. D. Bartlett: Tetrahedron Letters 1964, 1887.
D. R. Arnold, R. L. Hinman and A. H. Glick: Tetrahedron Letters 1964, 1425.
H. Sakurai, K. Shima and I. Aono: Bull. Chem. Soc. Japan 38, 1227 (1965).
S. Toki, K. Shima and H. Sakurai: Bull. Chem. Soc. Japan 38, 760 (1965).
D. Scharf and F. Korte: Tetrahedron Letters 1963, 821.
G. O. Schenck, W. Hartmann and R. Steinmetz: Chem. Ber. 96, 498 (1963).
R. Srinivasan: J. Amer. chem. Soc. 82, 775 (1960).
H. Morrison: J. Amer. chem. Soc. 87, 932 (1965).
N. C. Yang, M. Nussim and D. R. Coulson: Tetrahedron Letters 1965, 1525.
D. Bryce-Smith and A. Gilbert: Proc. Chem. Soc. 1964, 87.
D. Bryce-Smith and A. Gilbert: Tetrahedron Letters 1964, 3471.
C. H. Krauch, S. Farid and G. O. Schenck: Chem. Ber. 98, 3102 (1965).
J. Jennen: Bull. Soc. Chim. Belg. 46, 258 (1937); C. A. 32, 500 (1938).
J. J. Beereboom and M. Schach von Wittenau: J. Org. Chem. 30, 1231 (1965).
J. F. Harris, jr. and D. D. Coffman: J. Amer. chem. Soc. 84, 1553 (1962).
E. R. Bissell and D. B. Fields: J. Org. Chem. 29, 249 (1964).
E. W. Cook and B. F. Landrum: J. Heterocycl. Chem. 2, 327 (1965).
G. Büchi, J. T. Kofron, E. Koller and D. Rosenthal: J. Amer. chem. Soc. 78, 876 (1956).
D. Bryce-Smith, G. I. Fray and A. Gilbert: Tetrahedron Letters 1964, 2137.
H. E. Zimmerman and L. Craft: Tetrahedron Letters 1964, 2131.
J. A. Barltrop and B. Hesp: J. Chem. Soc. 1965, 5182.
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1968 Springer-Verlag Berlin · Heidelberg
About this chapter
Cite this chapter
Schönberg, A. (1968). Photochemical formation of four membered rings with one oxygen atom (Paternò-Büchi reaction). In: Preparative Organic Photochemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-87918-0_41
Download citation
DOI: https://doi.org/10.1007/978-3-642-87918-0_41
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-87920-3
Online ISBN: 978-3-642-87918-0
eBook Packages: Springer Book Archive