By W Parker;
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Dehmlow and E. V. Dehmlow, Annalen, 1973, 1753. M. Makosza and M. , 1973,3,305. L. Van Chau and M. Schlosser, Synthesis, 1973, 112. P. Weyerstahl, R. Mathias, and G. Blume, Tetrahedron Letters, 1973, 61 1. Three- and Four-membered Rings 39 An alternative to the two-phase system is to use higher temperatures and ethylene oxide in place of aqueous sodium hydroxide to remove the hydrogen halide generated in the reaction. This has been applied to the generation of gem-chlorofluoro- and difluoro-adducts,lo' but some of these adducts are unstable to the reaction conditions.
M. Hoiness, Org. Reactions, 1973,20, 1. F. D. Gunstone and B. S. Perera, Chem. and Phys. Lipids, 1973, 10, 303. L. Kohout and J. Fajkos, Coll. Czech. Chem. , 1973,38, 1415. 43 Three- and Four-membered Rings I i. CrO, ii, LiAlH, H (27 1 ) Scheme 23 I H (274) high (Scheme 24). The low reactivity of the 5,6-double bond is further illustrated by the regiospecific cyclopropanation' 2 3 of the pregnadienol (227). 125 R. Wiechert, D. Bittler, and G. A. Hoyer, Chem. , 1973, 106, 888. E. S. Balenkova and L.
This type of reaction has been reported previously. The benzothiepin derivatives (103; X = C1 or Br) cyclize in nearly quantitative yield62to the tricyclic compounds (104; X = C1 or Br). The influence of solvent and base strength on the cyclization was studied. A double intramolecular c y ~ l i z a t i o nhas ~ ~been used to synthesize the antitricyclohexane (106). Thus, the product (105) of photosensitized cycloaddition of trans-l,4-dichlorobut-2-ene to maleic anhydride, after conversion into the corresponding dimethyl ester, was treated with sodium hydride to furnish (106).
Alicyclic Chemistry Vol. 3 by W Parker;