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I. Budai, T. S. Khebnicova, and I. I. Petrusevich, Synthesis, 1978, 925. 33 R’ I a OCHCH(R’)CH2COR2 (PhS)3CLi+ R’CH=CHCOR2 + (PhS)3CCHCH2COR2 Reagents: i, CrC1,; ii, Cl+-Ag’-H,O Scheme 8 Skipped alkynes yield 1,4-diones on treatment with mercuric oxide and perchloric acid in aqueous d i ~ x a nA. 35 H O R ZX R4 KH , R ~1 C Z R 3~ ~ (5) R2X R4 X=OorS 31 32 33 34 3s Y. Oikawa, K. Sugano, and 0. Yonemitsu, J. Org. , 1978,43,2087. A. Hosomi, H. Hashimoto, and H. Sakurai, J. Org. , 1978,43, 2551. T.
E. Jung and R. W. Brown, Tetrahedron Letters, 1978, 2771. D. H. R. Barton, J. P. Kitchin, and W. B. S. Chem. , 197d, 1099. S. Cacchi, F. LaTorre, and G. Paolucci, Synthesis, 1978, 848. S. L. Huang, K. Ornura, and D. Swern, Synthesis, 1978,297; K. Omura and D. Swern, Tetrahedron, 1978,34, 1651. A. J. Mancuso, S. L. Huang, and D. Swern, J. Org. , 1978,43, 2480. 36 37 Aldehydes and Ketones react with DMSO to give the corresponding aldehydes and ketones in good yields. -A new regiospecific synthesis of a-thioketones has been described (Scheme l ) .
The coupled products (120) serve as useful precursors to insect pheromones. 189 lS6 lS7 lS8 lS9 L. A. Paquette, R. E. Moerck, B. Harirchian, and P. D. Magnus, J. Amer. Chem. ,1978,100, 1597. P. Place, M. L. Roumestant, and J. Gore, J. Org. , 1978, 43, 1001. R. H. Everhardus and L. Brandsma, Synthesis, 1978,359. H. Westmijze, H. Kleijn, and P. Vermeer, Tetrahedron Letters, 1978, 3125. Saturated and Unsaturated Acyclic Hydrocarbons < Me H \ / [Et/c=c\CH2CH2~ Me3SiC=CCH2CHzI (118) + c=c (119) Et Me Et 1 33 MgBr,LiBr.