โ Scribed by Fadila Derguini-Boumechal; Robert Lorne; Gerard Linstrumelle
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When allylmagnesium bromide (1.3 equiv.) was treated with octyl iodide (1 equiv.) and copper iodide (0.13 eqUiV.)
in ether at 0' for 1.5 hr, pure 1-undecene4 was obtained in 80% yield5. Without copper iodide, the reaction was very slow (22% of l-undecene, 66% of unreacted iodide after 28hr at OO).
The crotyl Grignard reagent', prepared from I-bromo-2-butene6 , treated with copper iodide ' and heptyl iodide (1 hr at -20ยฐ in tetrahydrofuran ) gave (85%)' a mixture (50: 50) of (E) and (Z) 2-undecene4. Less than 5% of 3-methyl-l-decene 4_b was formed.
3-methyl-2-butenylmagnesium chloride d is a very useful reagent for the introduction of the isoprene unit. This reagent, when treated with copper iodide and alkyl electrophiles undergoes alkylation in high yield exclusively in the a position. Thus, reaction of this organometallic (2 equiv.)
with copper iodide (0.2 equiv.) and heptyl iodide 8 , bromide, or tosylate 9
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