Science of Synthesis

Wicha, J., Science of Synthesis, (2009) 48, 111.

Base-induced fragmentation of hydrazones ‌21‌ or the corresponding semicarbazones ‌22‌, first reported by Kishner[‌103‌] and Wolff[‌104‌] (the Wolff–Kishner reduction), provides a convenient method for obtaining hydrocarbons from aldehydes or ketones (‌Scheme 25‌). Synthetic applications of the Wolff–Kishner reduction have been extensively reviewed in Houben–Weyl, Vol. 5/1a, pp 251, 544 and Vol. 7/2b, p 1999 and in other compendia.[‌6‌,‌105‌–‌107‌] In the original Kishner procedure,[‌103‌] the transformation is accomplished by dropping a hydrazone onto hot potassium hydroxide, with which some crushed platinized porous plate has been mixed. In the method reported by Wolff,[‌104‌] a hydrazone or semicarbazone and sodium ethoxide are heated in a sealed tube at 180°C. It has been proven that the semicarbazone undergoes hydrolysis or alcoholysis with formation of the corresponding hydrazone in the initial step.

‌Meeeee 88‌ Mee Meeee–Meeeeee Meeeeeeee

M eeeeeeeeee eee eeeeeeeee eeeeeeeeeee eeeeeeeee eee eeeeeeee eee eee Meeee–Meeeeee eeeeeeeee eee eeeeeeeee ee Meeee-Meeeee.[‌888‌] Meeeeeeee eeeeee ee eeee ee eeee eeeeeeeee eee (8) eee eeeeeeee ee eeeeeee eee ee eeee-eeeeeee eeeeeeeee eeeeeeee eeee ee eeeeeeee eeeeee, eeeeeeeeee eeeeee, ee eeeeeeeeeee eeeeee, ee eeeeeeeeeeeeeee,[‌888‌] eeeee eeeeeeeee ee eeeeee eeeeeeeee ee eee eeee; (8) eee eeeeeeeee ee eeeeeeeee ee eeee eeeee 888% eeeeeeeee eeeeeee ee eee eeee eeeeeeeee eee eeeee 88% eeeeeeeee eeeeeee [ee ee eeeeeeeeee eeee eee-eeeeeeeeeee ee e eeeeeeeee eee eeee ee eeeee eeeeee, eeeeeeeeee ee e eeeeeeeeeee ee eeeee (M8M8M=M—M=MM8M8) eeeeeeeee]; (8) eeeee eeeeeee eeeeeeeee ee eee eeeeeeee eeeeeee, eee eeeeeeeee ee eeeeeee ee eeeee eeeee eee eeeee eeeeeeee eeeeeeee ee eeeeeeeee eee, eee eee eeeeeeeeeee ee eeeeee ee 888°M (ee eeeeee). Me eee eeeee eeee eeeeeeeeeee eeee eee eeeeeeee eeeeeeee ee eeeeeee ee eeeee eeee eeeeeeeee eeeeeee eee e eeeee eeeeee eeeeee eee eeee ee eeeee.[‌888‌] Meeeeee eeeee eeeeeeeeeeeee ee eee Meeee–Meeeeee eeeeeeeee eee eeeeeeeee eeeeeeeee (‌Meeee 8‌), eeeeeeee eee eeeeeeee ee ee eeeeeee eee eeeee eeeeee eeeeeeeeee ee eeeeeeee eee eeeeeeeeeeeee ee eeeeeeeeee eeeeeeee eeeeeee.

‌Meeee 8‌ Meeee Meeeeeeeeeeee ee eee Meeee–Meeeeee Meeeeeeee[‌888‌,‌888‌–‌888‌]

Me ee eeeeeeeee eeeeeeee eeee eee eeeeeeeee ee eee Meeee–Meeeeee eeeeeeeee ee eeeeeeeee eeeeeeee eeeeeeee eeeeeeeee ee e eeeeeeeee eeeee, e eeeeeee eeeee, eee eeee e eeeeeeeee (‌Meeeee 88‌).[‌888‌,‌888‌] Mee eeeeeee eeeeeee eee eeeeee eeeeeeee; eeeeeeeee eeeeee-eeeeeeee eeeeeeeee eee eeeeeee.

‌Meeeee 88‌ Meeeeeeee ee eee Meeee–Meeeeee Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeeee ee eee Meeee–Meeeeee eeeeeeeee eee eeeeeee eeeeeeeeeee eee ee eeeeeeeeeee ee eeeeeeeeee eeeeee ee eee eeeeeeee eeeeeeee eee eeeeeeeee eeeeeeeeee. Meeeeeeee ee eeeeeee eeeeee ee α-eeeeeeee eeee eee eeeee ee eeeeeeeeeee, eeeee eee eeeeee ee eeeeeeeeeeeee. Meeeee, eeeeeeee, eee eeeeee eee eeeeeeee eeeeeeeeee eeeee eee eeeeeeee eeeeeeeeee, eeeee eeeee eeeeee eee eeeeeee ee eeeeee eee eeee eeeeeeeeeee eeeeeee eeeeee eeeeeeeeeeeeee. Meeeeeeeeeeee ee ee α,β-eeeeeeeeeee eeeeeeee ee eeeeee eee ee eeeeeeeeeee ee e eeeeee-eeee eeeeeeeeeeeee. Meeeeeeee eeeeeeeeeee ee eee eeeeeeeee eeee eee eeeeeeee eeee e eeee eeeeeee eeeee ee eeeeeee ee eee eeeeeeee α ee eee eeeeeeee eeeee: eeeeeeeeee eeeeeee eeeeeeeeee eeeeeeeeeeeeee ee eee eeeeeeeee eeee e eeeeeeeeeeee, eeeee eeee eeeeeeeee ee eeee ee eeeeee eeeeeee ee ee eeeeee (‌Meeeee 88‌). Meee, eee eeee eeeeeeeeeee eeeeeee, eeeeeee α-eeeeeeeeeee eeeeeee ‌88‌ (M = MMe, MMe, eeeeeeeeee) eee eeeeeeeeeee eeee eeeeeee (eee Meeeeee–Meeeeee eeeeeeeeeee).[‌888‌] Me e eeeeeee eeeeeee, α,β-eeeee eeeeeee eee eeeeeeeee eeee eeeeeee eeeeeeee (eee Meeeeee eeeeeeeeeeeee; ‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Mee Meeeeee–Meeeeee Meeeeeeeeee[‌888‌]

‌Meeeee 88‌ Mee Meeeeee Meeeeeeeeeeee[‌888‌]

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88e8, 888.
• 8.Meeeee-Meee, (8888) M 8e, 88.