Science of Synthesis

Drabowicz, J.; Krasowska, D.; Wicha, J., Science of Synthesis, (2009) 48, 258.

A tertiary or secondary nitro group in compounds ‌29‌ bearing electron-withdrawing substituents can be replaced by hydrogen (or deuterium) in good yields on treatment with 1.2 equivalents of tributyltin hydride (or deuteride) in refluxing benzene in the presence of 2,2′-azobisisobutyronitrile (0.1 equiv) to give alkanes ‌30‌ (‌Scheme 22‌).[‌112‌–‌114‌] Functionalities such as ketone, ester, cyano, and chloro groups are tolerated. Higher temperature and a large excess of tributyltin hydride enables the denitration of nonactivated secondary nitro groups.[‌115‌] Primary nitro groups are usually not affected.

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‌Meeeee 88‌ Meee-Meeeeee Meeeeeeee ee Meeeeeeeeeee eeee Meeeeeeeeee Meeeeee[‌888‌–‌888‌]

‌Meeeeeeeeee 88‌

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‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeeeee eeee Meeeeeeeeeee–Meeeeeeeeee Meeeeee[‌888‌]

‌Meeeeeeeeee 88‌

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Meeeeee ‌88‌; Meeeeee Meeeeeeee eee eee Meeeeeeeeee ee Meeeeeee Meeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeee eeeeeeeee eee eeeeee eeeee.

M eeeeeee ee eeeeeeee eeeee eeeeeeee ‌88‌ (88 eeee), Me8MeM (88 eeee), eee MMMM (8 eeee) ee eeeeeee (8 eM) (MMMMMMM: eeeeeeeeee) eee eeeeee ee 88°M eee 8–8 e. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee ee eee eeeeeee (eeeeee eee, eeeeee/MeMMe) ee ee eeeeeeeeeeee; eeeee: 88–88%.

Meeeeee ‌88‌; Meeeeee Meeeeeeee eee eee Meeeeeeeeee ee Meeeeeeee Meeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeee eeeeeeeee eee eeeeee eeeee.

M eeeeeee ee eeeeeeeee eeeee eeeeeeee ‌88‌ (88 eeee), Me8MeM (88 eeee), eee MMMM (8 eeee) ee eeeeeee (8 eM) eee eeeeee ee 888°M eee 8.8–8 e. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe) ee ee eeeeeeeeeeee; eeeee: 88–88%.

Meeeeee ‌88‌; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeee eeeeeeeee eee eeeeee eeeee.

Meeeee M: M eeee ee Me8MeM (8.888 eM, 8.8 eeee), MeMeM8 (8.888 eM, 8.88 eeee), eee MMMM (88 ee, 8.88 eeee) ee eeeeeee (8.8 eM) eee eeeee ee e eeee ee eee eeeee eeeeeeee (8.88 eeee) ee eeeeeee (8.8 eM). Mee eeeeeee eee eeeeeee ee 888°M (eee eeee) eee 8 e. Meeeeeeeee MMMM (88 ee, 8.88 eeee) eee eeee eeeee, eee eeeeeee eee eeeeeeeee eee 8 e. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 8e8, 8888.