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S. , 1981, 22,4217. g. 12' Reagents: i, 3NaH or 3NaOEt; ii, R'CHBrC0,H; iii, R2CHO; iv, H 2 0 Scheme 44 HO. A x o % R CO,H (X= H or CH20H) Reagents: i, H2NCMe2CH20H;ii, HCHO-KOH; iii, H' Scheme 45 '16 'I7 120 G. A. Russell, B. Mudryk, and M. Jawdosiuk, Synthesis, 1981,62. D. Liotta, C. Barnum, R. Puleo, G. Zima, C. Bayer, and H. S. Kezar, 111, J. Org. , 1981, 46, 2920;D. Saindane, C. Barnurn, H. Ensley, and P. , 1981,22,3043. R. Antonioletti, M. D'Auria, G. Piancatelli, and A. , 1981,22, 1041. R.

1981,46,647. V. Ratovelomanana and G. , 1981, 22, 315. G. Axelrad, S. Laosooksathit, and R. Engel, Synth. Commun.. 1981, 11, 405; J. Org. , 1981,46,5200. 76 Conjugated 1-bromo-dienes or -trienes can be prepared from the appropriate unsaturated carbonyl compounds. rB -& Reagents: i, CHzBrz-(C6H, ,)JW; ii, Zn-CH,CO,H E :Z= 55:45 Scheme 30 Vinylboronic acids, easily prepared by hydroboration of acetylenes, react with iodine monochloride at low temperatures to give good yields of E-vinyl iodides (Scheme 31).

M. Conia, Synthesis, 1981, 291; L. Blanco, N. Slougui, G. -M. , 1981, 22, 645. L. -M. Conia, Synthesis, 1981, 289. J. T. Gupton and C. M. Polaski, Synth. , 1981, 11, 561. 22 -- General a n d Synthetic Methods Lithium trialkylalkynylborates react stereoselectively with benzo- 1,3dithiolium fluoroborate to give functionalized vinylboranes (72) of mainly E- configuration (Scheme 37). g. g. '"" When the products are ketones they are contaminated with the corresponding saturated species. 102 The importance of the silyl group is that it can be relied on to remain in place during the d2-reaction, and then it can be removed, unmasking the conjugated carbon-carbon double bond.

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