1- or 3-Haloallyllithio and α-Halobenzyllithio Reagents

References

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• The product mixtures prior to purification by distillation or gas-phase chromatography showed the presence of only the halodienes subsequently isolated, thus indicating diene 3 to be the primary product and not the result of a thermal Cope rearrangement
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• Replacement of THF by ether interfered with reaction of allyl chloride, presumably because of slow metalation. However, treatment of the chloride with n-butyllithium in THF at -100° C for two hours afforded products 2b and 3 once again
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• Indeed no reaction was observed between these reagents and carbonyl compounds
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• Coates , R. M. and Robinson , W. H. 1972 . J. Am. Chem. Soc. , 94 : 5920
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• Josey , A. D. 1974 . J. Org. Chem. , 39 : 139 G. Büchi and R. M. Freidinger, J. Am. Chem. Soc., 96, 3332(1974); J. Eriksen, K. Krogh-Jespersen, M. A. Ratner, and D. I. Schuster, ibid., 97, 5596(1975)
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• The use of one equivalent of LDA afforded the same results
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• The same reaction with crotyl bromide yielded a mixture of olefins (75%) containing mostly (80%) 4-bromo-2E, 6E-octadiene: 1H NMR (CDCl3) δ 1.4–1.8 (m, 6, Me2), 2.3–2.8 (m, 2, CH2), 4.2–4.7 (m, 1, BrCH), 5.2–5.7 (m, 4, olefinic methines); 13C NMR (CDCl3) 17.4, 17.9 (C-1, C-8), 42.4 (C-5), 55.7 (C-4), 127.0 (C-2), 128.2, 128.4 (C-3, C-7), 132.4 (C-6)
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• Its gc/ms analysis revealed each gc component in the form of m/e 136 (M+), 93 (base)
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• This component could be purified also by chromatography on neutral Woelm alumina (activity I) and elution with pentane
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