References
- Liu , H. J. , Valenta , Z. , Wilson , J. S. and Yu , T. T. J. 1969 . Can. J. Chem. , 47 : 509
- Hunter , N. H. , MacAlpine , G. A. , Liu , H. J. and Valenta , Z. 1970 . Can. J. Chem. , 48 : 1436
- Ho , P. -T. , Lee , S. F. , Chang , D. and Wiesner , K. 1971 . Experientia , 27 : 1377
- For a general discussion of synthetic utilities of the compounds of the type 2, see ref. 2. Specific examples may be found in ref. 1 and 5
- Bergstrom , D. E. and Agosta , W. C. 1974 . Tetrahedron Letters , : 1087
- House , H. O. “ Chapter 9 ” . In Modern Synthetic Reactions , 2nd ed. , Menlo Park , Calif. : W. A. Benjamin, Inc. .
- Though no examples were given, the method cited in ref. 3 is conceivably applicable to α,β-unsaturated ketones without enolizable γ-hydrogen atom
- Corey , E. J. , Bass , J. D. , LeMahieu , R. and Mitra , R. B. 1964 . J. Amer. Chem. Soc. , 86 : 5570
- All the yields given are for isolated products and have not been optimized
- A pure sample, m.p. 116–7°C (ether-pet, ether), displayed the following spectral data: ir (CHC13) 1770 and 1712 cm−1; nmr (CDCl3) δ 2.60–3.55 (m, 3H), 2.32 (s, 2H), 2.20 (d, J = 15 Hz, 1H), 1.79 (d, J = 15 Hz, 1H), 1.51 (s, 3H), 1.10 (s, 3H), and 0.90 (s, 3H); M+ 196.1104 (Calcd. for C11H16O3: 196.1100). Its stereochemical assignment follows from the fact that Baeyer-Villiger oxidation (which is known to proceed with retention of configuration11) of 11 with m-chloroperbenzoic acid gave the same lactone as the only product
- Turner , R. B. 1950 . J. Amer. Chem. Soc. , 72 : 878
- Harris , R. L. N. , Komitsky , F. Jr. and Djerassi , C. 1967 . J. Amer. Chem. Soc. , 89 : 4765
- Marvell , E. N. and Stephenson , J. L. 1955 . J. Amer. Chem. Soc. , 77 : 5177
- As an exceptional case, ester (19% yield) was isolated, along with the normal products (lactone and acid), directly from photoadduct [→→ (')] in the hydrolysis-oxidation step. After removing , the mixture of lactone and acid was subjected to base treatment in the presence of isopropyl iodide; when methyl iodide was used, the reaction gave largely
- Liu , H. J. and Ogino , T. 1973 . Tetrahedron Letters , : 4937
- Djerassi , C. , Engle , R. R. and Bowers , A. 1956 . J. Org. Chem. , 21 : 1547