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Corey, H . Yamamoto, D. K. Herron, and K. Achiwa, J . Amer. Chem. , 1970,92,6635. lS5Thus the allylic acetate (245), on treatment with X, Y,Z = H or alkyl Scheme 15 lithium dimethylcuprate, stereoselectively gave (246), which contains the juvenile hormone skeleton. la7Thus (251) is converted into the J. Corey and H. Yamamoto, J . Amer. Chem. ,1970, 92, 6636. Schlosser and K. F. Christmann, Synthesis, 1969, 38; E. J. Corey, J. I. Shulman, and H. Yamamoto, Tetrahedron Letters, 1970, 447. lR5 R. J.

Aliphatic, Alicyclic, and Saturated Heterocyclic Chemistry 22 / FYMe oI,Me):,/-< I (79) z: ( ((yMe):H \ H (80) Br I3U" NaOMe OM'-OM' H '\\ /c=c\ / H Bun H+ '\\\ -B /c=c\ /H Bun I chloride (81) is formed, which readily cyclizes to the benzothiophen (82). 72 Addition of HX to the double bond is trans and provides a general method for PhClC II CClPh II Ph l' 72 (83) T. J. Barton and R. G. Zika, J . Org. , 1970, 35, 1729. P. E. Peterson, R. J. Bopp, and M. A. Ajo, J . Amer. Chem. ,1970,92, 2834. 1° In the presence of superacids, alkynes generate vinyl cations which are trapped by carbon monoxide.

R. O'Connor and F. N. Jones, J . Org. , 1970,35,2002. M. Jautelat and K. Ley, Synthesis, 1970, 593. lo3K. M . Nichols and R. Pettit, Tetrahedron Letters, 1971, 3475. lo4 S. Kobayashi, M. Shinya, and H. Taniguchi, Tetrahedron Letters, 1971, 71. lol lo2 34 Aliphatic, Alicyclic, and Saturated Heterocyclic Chemistry H 0. 011 (CO),Co- - :co(co), (141) (144) R' = RZ = ? (146) R1 = Me, R! 'C=G=CPhp I Br (145) \L Me 35 A study of the metallation of 1-phenylpropyne (149) has shown that the dianion produced is different from that prepared from 3-phenylpropyne and Acetylenes, Allenes, and Olefins PhCH~C~CII -

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An Outline of Geophysical-Chemical Problems (1920)(en)(10s) by Sosman R.B.

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