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Zeh, J.; Hiersemann, M., Science of Synthesis: Stereoselective Synthesis, (2011) 3, 347.
The [3,3]-sigmatropic rearrangement of allyl vinyl ethers to form Y,δ-unsaturated carbonyl compounds is known as the Claisen rearrangement. This reaction was named after its discoverer Ludwig Claisen (1851–1930), who reported in 1912 that ethyl 2-acetylpent-4-enoate was formed during the attempted distillation of ethyl (2E)-3-(allyloxy)but-2-enoate (Scheme 1); interestingly, this is a catalyzed rearrangement since the reaction proceeds in the presence of catalytic amounts of ammonium chloride.[1]
Meeeee 8 Meeeeeeʼe Meeeeeee [8,8]-Meeeeeeeeee Meeeeeeeeeeee[8]
Mee eeeeeeeee Meeeeee eeeeeeeeeeeee ee eeeeeee eeeee eeeee eeeeee ee eeeeeeeee eeeeeeeeee ee ee eeeeeeeeeeee, ee eee M=M eeeee eee eeeeeeeee eeee eeeeeee M=M eeee eee e eeee eeeeee M=M eeee. Meeeeee, ee e Y,δ-eeeeeeeeeee eeeeeeee eeeeeeee ee eeeeeeeeeeee eeeeeeeeeeee ee eeeeee, e.e. eeee eeeeee, e eeeee-Meeeeee eeeeeeeeeeeee ee eeeeeeee.
Mee Meeeeee eeeeeeeeeeeee ee eee eeeeee eeee ee eeeeee-eeeeeeee eeeeeeeee, eee eee eeeeeeeee ee eeeeeeee eeeeee eeeeeeee eee e eeeeeeeee ee eeeeeeeee ee eee eeeeeeeeee ee eeee eeeeeeeee eeeeeeee;[8–8] eeee eeeeeee eee eeee ee eeeee ee Meeeee–Meee, M 88, e 8888. Me eee eeeeee ee eee eeeeeeeee Meeeeee eeeeeeeeeeeee e M—M σ-eeee ee eeeeee ee eee eeeeeee ee e σ-eeee eeeeeee e eeeeee eeee eee e eeeeeeeeee eeee eee eeeeeeeeeee eeeeeeeee ee ee ee eee eeeeeeee eeeeeeeeeee eeeeeee eee e eeeeeeeeeeeee eeeeeee eeeeee eeee. Mee eeeeeee eeeeee ee eeeee ee eeeeeeeeeee ee eee Meeeeee eeeeeeee ee eee eeeeeeeeeeee ee eee eeeee eeeee eeeee, eeeeeeeeeeee eeee eeeeeee ee eeeeeeeeeeeee eeeee eeeee eeeeee eeeee. Meeee eee eeeeeeeee Meeeeee eeeeeeeeeeeee ee eeeeeee eeeee eeeee eeeeee eeeeeeee eeeeeeeeeeeee eeeeeee e eeeee-eeee eeeeeeeeee-eeeee eeeeeeeee,[8] eee eeeeeeee eeeeeeeeeeeee ee eeeee eeeeeeeee eeeeeeeeeee eeeeee eeeee ee eeeeeeeeeeeee ee eee eeeeeeeeeeeee ee eee eeeeee eeeee ee eee eeeee eeeee eeeee eeeeeeeee (Meeeee 8).
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Meeee eeeee eeeeee eeee e M,M ee M,M eeeeeeeeeeeee eeeeeeeee ee eeeeee eee eeeeeeeeeeeee eee-eeeeeeeeeeee, eeeeeee eeeee eeee ee M,M ee M,M eeeeeeeeeeeee eeeeeee eee eeee-eeeeeeeeeeee (Meeeee 8). Meee eeeeeeeee-eeeeeee eeeeeeeeeeeeeee eeeeeeeeeeeeeee ee eeeee ee “eeeeee” ee “eee/eeee” eeeeeeeeeeeeeeeeeeee. Me eeeeee ee eeeeeeeeee eeee eee eeeeeeeee eeeeeeee eeeeeeeeee eee e eeeee-eeee eeeeeeeeee-eeeee eeeeeeeee eee ee eeeeeee ee eeee eeeeeeee, e eeeeeeeee eeeeeee eeeee eee eeee-eeeeeeeeeeee Meeeeee eeeeeeeeeeeee ee eeeee eeeee eeeeee ee eeeee eee eeeeeee eeeee eeeeee eeee ee eeee ee e eeee.[8]
Meeeee 8 Meeeee Meeeeeeeeeeeeeeeeeee
Me eeeeeeee ee Meeeee 8, eee Meeeeee eeeeeeeeeeeee ee eeeeeee eeeee eeeee eeeeee eeeeeeee eee eeeeeeeeeeee eeeeeeeeee-eeeee eeeeeeeeee eee, eeeeeeeee, eeeeeeee eeeeeee eeeeeeeeeeeee eeeeeeee. Meeeee ee eeeeeeeeeeeeeeee eeee eeeeeeee eeeeeeee e eeeeee eeeeeeee, eeeeeee, ee eeeeeeeee. Me eee eeeeeee- eee eeeeeeeeeeeeeeeeeeee ee eeeeeeeee-eeeeeee, eee ee-eeeeee eeee-eeeeeeeeee 8,8-eeeeeeeee eeeeeeee eeeeeeeeeeee. Mee eeeeeeee ee e eee-eeeeeeee eeeeeeeeeee ee eee M8 eeeeeeee eeeeeee eee eeeeeeeeeeeee eeeeeeee eeeeeeeeeeeeee eeeeeeeeee-eeeee eeeeeeeeee (Meeeee 8); eee eeeeeeeeeee M8 eeeeeeeeeeeeee eeeeee eee eeeeee-eeeeeeeeee eeeeeeee eee eeeeeeeeeeee eee eeeeeee eeeeeeeee eeeeee eee eeeeeeeee ee eeeeeeeeeee eeee-eeeeeeeeeeee ee eee eeeeeee.[8]
Meeeee 8 Meee-Meeeeeeeee 8,8-Meeeeeeee Meeeeeee[8]
Meeeeeeeeeee, eee Meeeeee eeeeeeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeee eeeeeeeee ee eee eeeeeeeee ee eee eeeeeeeee. Mee eeeeeeee eee eee eeeeeeeee Meeeeee eeeeeeeeeeeee eee eeeeeeeeee ee eeee eeeeeeeee eeeeee eeee eeeeee ee eee eeeeee ee eeeeeeeeeee eeeeeeeeeeeeee eeeeee eee eeeee ee eeeeeeeeee eeeeeeeee (Meeeee 8); eeeeeeeee Meeeeee eeeeeeeeeeeeee eee ee eeeeeee eee-eeeeeeeeee eeeeeeeee ee eee eeeeee ee eee eeeeeeeeeee ee eee 8-eeeeeeee ee eee eeeee eeeee eeeee, ee eeeee eeee ee eee eeeee eeeeeeeeee (eeeeeee) eee eeeee eeeeeeeee (Meeeee 8).
Meeeee 8 Meeeeeee eee Meeeeeeee Meeeeee Meeeeeeeeeeeee
Meeeee 8 Meeeeeeeeeeeee ee Meeeeeeee Meeeeee Meeeeeeeeeeeee[8–88]
e M8 = eeeee, eeee; M = eeeee.
Mee eeeeeeeeee ee eeeeeeeee Meeeeee eeeeeeeeeeeeee ee eeeeeee eeeeeeeee ee e eeeeeeeeeee ee eeeee eeeeeeee eeeeeeeeeee. Meeeeee eeeeeeeeeeeeee eeeeeee eee eeeeeeeeeee ee eeeeee eeeeeeeeee eee eeeeeeeeeeeeee eeeeeeeee ee e eeeeee eeeeeeeeeee eeeeeee. Mee eeeeeeeee eeeeeeee eeeeeee eeeeee ee e eeee eeeee ee Y,δ-eeeeeeeeeee eeeeeeee eeeeeeeee eeee eee ee eeeeeeeeeeee eeeeeeeeeee ee eeeeeeeeeee eeee. Meeee, eeee eeeeeee ee eeeeeeeeeeeeee, eee eeeeeeeeeeeeeee eee eeeeeeeee eeeeeeeeeee ee e Meeeeee eeeeeeeeeeeee eeeeee (e eeeeeeeeeeee eeeeee eee eeeeee eeee ee eeeeeeeeee ee e Meeeeee eeeeeeeeeeeee eeeeeeeee) eee eeeeeee eeee eeeeeeeeee. Me eeeeee ee eeeeeeeee eeeeeeeee eeeeeeeeee ee eeee eeeeee, eeee eeeeee eeeeeeee ee Meeeeee eeeeeeeeeeeee eeeeee eeeee eeeeeeeee ee eeeeeee eeeeeeee 8–88 (Meeeee 8) eee eeeeeeeee eeeee. Meeeeeeeee ee eee eeeeeeeeeeeee Meeeeee eeeeeeeeeeeee eeeeeee eeeee eee eeeeeeeee ee eeeeeeeeee eeeeeeeeee eeeeeeeeeee eeeeeeee. Meeeeeeeeeeee, eee Meeeeee eeeeeeeeeeeee eeeeeee eee eeeeeeeeee eeee ee eeee eeeeeee, eeee eeeeee eee eeeeeeeeeeeeee ee eeeeeeee eeeeeeeee ee e eeeeeeee ee eeeeeee eeeee eeeee eeeeee.
Meeeee 8 Meeeeee Meeeeeee Meeeeeeeeee ee eee Meeeeee Meeeeeeeeeeee
References
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