Alicyclic Chemistry Vol. 3 by W Parker;

By W Parker;

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Bertrand, Bull. chim. France, 1973,2340. J. Gore and A. Doutheau, Tetrahedron Letters, 1973, 253. M. S. Newman and Z. U. Din, J. Org. , 1973,38, 547. H. E. Simmons, T. L. Cairns, S. A. Vladuchick, and C. 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).

Offen. 2219710 (Chem. Abs.. 78, 29 312). J. Dolansky, V. Bazant, and V. Chvalovsky, Coll. Czech. Chem. , 1973, 38, 3816. E. Lee and D. W. S. Perkin ZZ, 1973,437. Three- and Four-membered Rings 49 It is, perhaps, worth bearing the above in mind in considering the results of Moss and M a l l ~ n who , ~ ~have ~ examined the possibility of synergism in the addition of dichlorocarbene from (243) to oxygenated cyclohexenes. Earlier, it had been suggested that dichlorocarbene-oxygen co-ordination could be responsible for a three-fold increase in the rate of attack on the double bond, but some evidence to the contrary was presented by Moss and further results have now been reported for the exo-methylenecyclohexanes (245a-d).

Miyamoto, Tetrahedron, 1973, 29, 3819; G. Pattenden and M. Bullivant, Pyrethrum Post, 1973,12, 64. 86 Sensitized photolysis of the parent allyl halides (169; X = C1 or Br) affords the cyclopropanes (170; X = Cl or Br) in 10% yield, whilst the butenyl chloride (171) gives the allylic isomer (172) and isomeric cyclopropanes (173) and (174). By using a mixed acetonitrile-acetone solvent it was found possible to achieve essentially quantitative conversion into halogenocyclopropanes. Cinnamyl chloride and its isomer (3-chloro-3-phenylprop-1 -ene) both cyclize to trans-2-phenylchlorocyclopropane initially, but prolonged irradiation produces a photostationary state containing an approximately equimolar amount of the cisisomer.

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