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Extra info for Aliphatic, Alicyclic and Saturated Heterocyclic Chemistry Volume 1 Part 1 a review of the literature published during 1970 and 1971
G7 65 66 13’ G. Wilke and H. Miiller, Annalen, 1960, 629, 222. G. Zweifel and R. L. Miller, J . Arner. Chem. ,1970, 92, 6679. G . ZweifeI, G. M. Clark, and C. Whitney, J . Arner. Chem. ,1971, 93, 1305. Acetylenes, Allenes, and Olefins 21 Monohydroboration of terminal alkynes with bulky hydroboranes (76) places the boron exclusively at the terminal position of the triple bond. Addition to unsymmetrically disubstituted alkynes is markedly affected by the triple bond substituent size. 68 Hydroboration of hex-1-yne with bis (trans-2-methylcyclohexyl)borane (77) gives the vinylborane (78).
Chen, J . Amer. Chem. ,1971, 93, 2562. P. Battioni, L. -C. Raymond, and Y. Vo-Quang, Compr. , 1970, 271, C, 1468. lSea 140 M. C . Caserio, SeIectiue Org. , 1970, 1, 239. L. R. Byrd and M. C. Caserio, J . Amer. Chem. ,1970, 92, 5422. Acetylenes, Allenes, and OleJiris 45 products are also obtained. None of the products isolated using optically active penta-2,3-diene are optically active. l4l Addition of hypochlorous acid to allenic hydrocarbons, an electrophilic attack, leads, in all cases, to the placement of the chlorine on the central carbon atom and the OH group on the more substituted of the allenyl ~ a r b 0 n s .
Medvedeva, L. P. Safronova, and V. K . Voranov, Zhur. org. , 1970, 6, 2377 (Chem. , 1970,14, 64 134g). E. J. Corey, N. W. Gilman, and B. E. Ganem, J . Amer. Chem. , 1968, 90, 5616. -H. Bonnet and F. Bohlmann, Chem. , 1971, 104, 1616. H . Gopal and A. J. Gordon, Tetrahedron Letters, 1971, 2941. D. B. J. Easton and D. Leaver, Chem. , 1965, 585. Acetylenes, Allenes, and Olefins 33 bearing electron-withdrawinggroups and the -C(==S)Sunit are necessary for the success of this reaction. Thus (136) reacts to give (137), but the SS'ethylene dithiocarbonate was unreactive.