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48.1.3.2.4 Method 4: Alkanes from Iodoalkanes

DOI: 10.1055/sos-SD-048-00062

Margaretha, P.Science of Synthesis, (200948157.

Several methods that allow the reduction of haloalkanes (R1X; X=Cl, Br, I) to alkanes in general have already been discussed in Sections 48.1.3.2.2.2 and 48.1.3.2.3.1. As for bromoalkane reductions, the most commonly employed reducing agent for CI to CH transformations is tributyltin hydride, generally in combination with 2,2-azobisisobutyronitrile as an initiator, the reactions usually being run in benzene or toluene at 80°C. This is illustrated by the conversion of 2-(3-iodopropyl)-2-(methoxymethyl)indan-1-one (33) into indanone derivative 34 (Scheme 16).[‌10‌]

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Meee eeeee, eee eeeeeeeeeee eeeeeeeeeee eeeeeee, eeeeeeeeeeeeee, eee eeeeee eeeeee eeee eeeeeeeee ee ee eee eeeeeeeeeee ee eeeee eeeeeeeeeeee (e.e., ee eeeeeeeeeeeeeee ee 8°M).[‌88‌] Meeeeee-eeeeeeeee eeeeeeeee eeeeeeee, eeeee eee eeeeeeee ee eee eeeeeeee ee ω-(eeeeeeeee)eeeeeeeeeeee eeee eeeeeeeeeeeeeeeeeeeeeeeeeeee, eee ee eeee ee eeeee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeee eeeeeeee eeee eee, ee eee eeeeeeeeeeeeee eeeeeee ee eeeeee eeeeeeeee ee eeeeeeeeee. Mee eeeeeee eee eeee ee eeeeeeeeeee ee eeeeee eeeeeeeeeee eeeeeeeee ee eee eeeeeee.[‌88‌] Mee eeeeee eee eee eeeeeeeeee ee 8-eeeeeeeeeee-8-eee (88) eeee eeeeeee-8-eee (88) ee eeeee eeeeee eeeeeee eeeeeeeeeee eeeeeee ee eeee eeeeeee eee eeee eeeeeee, (e.e., 8888%), eee eee eeeeee ee eeeeeeeee eeeeeee ee eeeee ee e eeeeee ee eeeeee 88 ee eee eeeeee eeee (Meeeee 88).

Meeeee 88 Meeeeeeee eeee e Meeeeee-Meeee Mee Meeeeee[‌88‌]

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Meeeee 88 Meeeeeeeeeeee ee MM Meeee[‌88‌,‌88‌]

Meeeeeeeeeeee, eeeeeee eeee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeee ee eeeeeeee-eeeeeeeee eeeeeee (e.e., eeee eeeeeee eeeeeeeeee eeeeeeee, eeeee, ee eeeee eeeeeeeeeeeeeee) eee ee eeeeeeeeeee eeeeeeeeeee ee eeeee eeee ee eee eeeeeeee ee eeeeeeeee eeeeeee ee eeeeee(MM) eeeeeeee ee e eeeeeeee eeeee.[‌88‌] Meeeeeeee eeeeeeee (e.e., eeeeeee eeeeeeee eeeeeee[‌88‌] ee eeeeee eeeeeeeeeee)[‌88‌] eeee eeee ee ee eeeeeeee eeeeee eeee eeee ee eeee ee eee eeeeee eeeeeeee eeeeeeeeee. Meeeeeeeeeee, eeeeeeeeee eeee ee eeeeeeeee eeeeeeee eee eeee eeeee ee eeeeeee eeeeeee MM eeeee eeee MM eeeee, ee eeeeeeeeeee eee eee eeeeeeeeee ee eeeeeeeeeee 88 eeee eeeeeee 88 (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeeeeeeee eeee Meeeeeeeee Meee[‌88‌]

Meeeeee, ee eeeeee ee eeeeeeeee eeee eee eeeeeeeeeeeeeeee ee eeeeeeeeeee eeeeeee eeeeeee, eeeeeeee eeee eeeeeeeeeee eee eee eeeee eee ee e eeeeeeeee eeeee. Me 8888, eeeeeee ee eee eeeeeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeee ee eeeeeeeeeeeeeee ee eeeeee eeeeeeeeee eeee eeeeeeeee.[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-(Meeeeeeeeeeee)-8-eeeeeeeeeee-8-eee (88):[‌88‌]

Me8MeM (8.88eM, 8eeee) eee MMMM (88ee, 8.88eeee) eeee eeeee ee e eeee ee eeeeee 88 (888ee, 8.88eeee) ee eeeeeee (88eM) eeeee ee eeeee eeeeeeeeee. Meeee eeeeeeeee eee 8e, eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (Me8M/eeeeeee 88:8) ee eeeeee ee eee; eeeee: 888ee (88%).

Meeeeeee 8,8,88-Meeeeeee-β-M-eeeeeee-eee-8-eeeeeeeeeeeeeeeee (88):[‌88‌]

M eeee ee eee 8-eeee eeeeeeee 88 (88ee, 8.888eeee) eee eeeeeee MeMM (8 eeeee) ee MeMM (8eM) eee eeeeeeeee ee eeeeeeeeeeeeee eeeeeeeeee (888eMe M8, 88% Me/M) eeeee eee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeee eeeeeeee eee eeeeeeee ee MMM (MeMMe/MeMM 88:8). Mee eeeeee eeee eeee eeeeeeee eee, eee eeeeeeee eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/MeMM 88:8); eeeee: 88ee (88%).

8,8,8,8,8,8,88,88,88,88,88,88,88,88,88,88,88-Meeeeeeeeeeeeeeeeeeeeeeee-8-ee (88):[‌88‌]

MeMMM8 (8.8e, 88eeee) eee 88% Me/M (8e) eeee eeeee ee e eeee ee eeeeee 88 (88e, 88eeee) ee MeMM (888eM) eee eee eeeeeee eee eeeeeeeeeeee eee 88e ee ee eeeee M8 (888eMe). Meeee eeeeeeeeee eee eeeeeee eee eeeeeee, eee eee eeeeeee eee eeeeeeee ee Meeeeeeee eeeeeeeeeeee (88888°M/88Me); eeeee: 88.88e (88%); ee 88°M.

Meeeeeeeeeeeeee [88, M8=(MM8)8MMe]:[‌88‌]

Me e 888-eM eeeee, e eeee ee 8-eeeeeeeee eeeeee eeeee [88, M8=(MM8)8MMe; 88.8e, 88eeee], MeM8MM8M8M (88.8e, 888eeee), eee MMMM (8.88e, 88eeee) ee 88% ee MeMM (888eM) eee eeeeeeee eee 88eee eee eeee eeeeeee ee eeee ee ee. M8M (888eM) eee eeeee, eee eee eeeeeeeeeee eeee eee eeeeeeeee eeee eee eeeeee. Mee eeeee eeeee eee eeeeeeeee eeee e Meeeeee eeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeee; eeeee: 88%.

References


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