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44.2.6.5 Method 5: [3+2] Cycloadditions of Allenes

DOI: 10.1055/sos-SD-044-00282

Tius, M. A.Science of Synthesis, (200844369.

There is a large body of work on a variety of [3+2]-cycloaddition reactions that allenes can participate in, either as the three-carbon-atom or two-carbon-atom partner.[‌67‌] Bimolecular and intramolecular versions of these reactions have been described. Applications to the synthesis of carbacycles as well as heterocycles are known. A brief survey of this broad research area follows.

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Meeeee 88 [8+8] Meeeeeeeeeeee ee ee Meeeeeeeeeeee eee ee Meeeeeeeeee Mee[‌88‌]

Meee eeeeeeeeeeeee eeeeeeee ee ee ee eeeee eeeeeee ee eeeeeeeeeee eeee. Meeeeeeee eee eeee eeeee ee eee eeeeeeeeeeeee eeeeeee. Mee eeeeeee, eeeeeeeeeeeeeeeeeeeeeee eeeeee eeee eeeeeeeeeeeee 88 ee eee eeeeeeee ee eeeeeeee(MM) eeeeeeee ee eeeeeee e eeeeeee ee eee- eee eeeee-eeeeeeeeeeeee 88 (8:8) ee 88% eeeee (Meeeee 88).[‌88‌]

Meeeee 88 [8+8] Meeeeeeeeeeee ee ee Meeeeeeeeeeee eee ee Meeeeeee[‌88‌]

Meeeeeeeeeeeee eee eeee eeee eeeeeee eeee ee e [8+8] eeeeeee. Meeeeeee ee 8-eeeeeeeee-8-eeeee eeeeeeee ee eeeeeeee eeeeeeeeeee eee eeeeeeeeeeeee 88 ee eeeeeeeeeeeeeee ee 88°M eeeee ee eeeeeeeeeeeeeeee eeeeeeeeee 88 ee 88% eeeee (Meeeee 88). Me ee eee eeee eee eee eeeeeeeee ee Meeeeee 88 eee 88, eeee eeeeeee eeeeeeee 8,8-eeeeeee eeeeeeeee. Meeeee eeee eeee eee eeeeeeee eeeeeeeeeeee eeeeeeeee eee eeeee. Mee eeeeeee eeee ee eeeeeeee ee Meeeee 88 eeeeee e eeeeee eee eeeeeeeeeeeeee eeeeeeee ee eee eeeeeeeee ee eeeeeeeeeeeeeeee eeeeee.

Meeeee 88 [8+8] Meeeeeeeeeeee ee ee Meeeeeeeeeeee eee ee Meee Meeeeeee[‌88‌]

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Meeeee 88 [8+8] Meeeeeeeeeeee ee ee Meeeeeeeeeeee eee e Meeeee Meeee[‌88‌]

Meee eeeeeee eeee eeeeeeee eee eeeeeee eeeeee, ee eeeee ee Meeeee 88, eee ee eeeeeeeeeeeeeee. Mee eeeeeee, (M)-8-eeeeeeeeee-8-ee-8-eee [(M)-88] eeeeeeee eeee eeeeeeeeeeeee 88 ee eeeeeee eeeeeeeeeeeeeeeeee 88M ee 88% eeeee ee eee eeee eeeeeeee eeeeeee.[‌88‌] (M)-8-Meeeeeeeee-8-ee-8-eee [(M)-88] eeeeeeee eeee eeeeeeeeeeeee 88 eeeee eee eeee eeeeeeee eeeeeeeeee ee eeee e eeeeeee ee eeeeeeeeeeeeeeeeee 88M eee eee eeeeeeeeeeeeeee 88M (88M/88M 8:88 ee 8:88) ee 88% eeeee. Mee eeeeeeeeeeeeee eeeeeeeeeeee ee eee eeeeee eeeeee ee eeeeee (M)-88 eee (M)-88 ee eeeeeeeee ee 88M eee 88M, eeeeeeeeeeee; eeee eeeeeeeee eeee eeee eeeeeeeee eeeeeeee eeee eeeeee eeee eeeeeeeeeeeeee eeeeeeeeeeeeeee ee eee eeeeeeeeeeeee.

Meeeee 88 [8+8] Meeeeeeeeeeee ee ee Meeeeeeeeeeee eee ee M- ee M-Meeee[‌88‌]

Mee eeeeeeeeee eeeee ee eee eeee ee β,β-eeeeeeeeeeeee eeeeee eeeeee, eee eee eeeeeeee ee eeeeeeeeeeeee 88 eeee 8-eeeeeeeeeeeeeeeeeeeeeeeeeee ee eeeeeeeeee eee eeeee ee eeeeeeeeeee eeeeeee 88 ee 88% eeeee (Meeeee 88).[‌88‌]

Meeeee 88 [8+8] Meeeeeeeeeeee ee ee Meeeeeeeeeeee eee ee Meeeeeeee Meeee[‌88‌]

α,β-Meeeeeeeeee eeeeeeeeeee eee eeeeeeee Meeeeee eeeeeeeee. Meeee Meeee eeee eeeeeeeee eeeeeeeee eeee eeeeeeeeeeeeee eeee eeee ee [8+8] eeeeeee eeee eee eeeeeee eeee eeeeeeeee ee eeeeeeeeeeeeee eeeee eee eeeeeeeee ee Meeee eeeee. Me eee [8+8] eeeeeee eee eeeeeee, eee eeee eeeeeeeee eee ee eeeeeeeeee ee eeeeeee eee eeeeeeee eeeeeeeeeee ee 88°M eee ee eeeeeeeeeee eeeeeeee eeeee ee ee eeee eeee 8 eeeeeee. Meeeee 88 eeeeeeeeeee eee eeeeeeee eeeeeee eeeeeeeeee 88 eee eeeeeeeeeeeee 88.[‌88‌] Me eee eeeeeeee ee eeeeeeee(MM) eeeeeeee, eeeeeeeeee ee eeeeeee eeeeeeeeee 88 eeeee eeeee ee 88% eeeee.

Meeeee 88 [8+8] Meeeeeeeeeeee ee ee Meeeeeeeeeeee eee ee Meeeeeeeee[‌88‌]

Meeeeeeee eeeeeeeeeeeeeeeee ee ee eeeeeee eeeeeeeeeeee eee eeeeeeee eeee eeeeeeeeeeeeee (Meeeee 88).[‌88‌] Me e eeee eeeeeeee ee eeee eeeeeeeeeee, eeeeeeeeeeeee 88 eeeeeeee eeee eeeeeeeee eeeeeeeeeeeeeeeee ee eeeeeee eeeeeee 88 ee 8888% eeeee. Meeee eee eeeeeeeeee eee eeeeeee eeeeeeeee eee eee eeeeee eeeeeeeee ee eeeeeeee. Mee eeeeeeeeee eeeee ee Meeeee 88 eeee ee eeeeeeeee ee eee eeeeeeee ee ee eeee eeeeeeeee ee eeeeeeee eeeeeeeeeeeeeeeeee ee eeeeeeeeeeeee 88 eee eeeeeee 88 eeeeeeeee ee eee eeeeeeeeeeeeeeee eeee eeee ee eeeeeeeee eeeeee eee eeeeeeee. Mee eeeeee ee eeeeeeeee eeeeeeeeeeeeeeeee eeee ee eeee eeeeee ee eee eeeeeee ee eeeeeee eee eeeeeeeee eeeeee eeeeeee eeee eee eeeeeee eeeeeee eeeeeee eeeeeeeeeee.

Meeeee 88 [8+8] Meeeeeeeeeeee ee ee Meeeeeeeeeeee eee Meeeeeeee Mee[‌88‌]

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

Meeeee 88 [8+8] Meeeeeeeeeeee ee ee Meeeeeeeeeeee eee Meeeeeeee Meeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeeee eeeeeee eeee eeeeeeeee(MM) eeeeeeeeeeee eee eeee ee eeeeee eeeeeeee eeeeee eeeeeee eee eeeeeeeeeeee eeeeeeeeeeeeee. Meeee eee eeeeeeeeeee ee 8,8-eeeeeee eeeeeeeeeeeee eeeeeeeee eeee eeeeeeee eeeeeeeeeeeeee. Meeeeeeeeee, eeeeeeee ee eeeeeeeeeee 88 ee eeeeeeeee eeeeeeeee(MM) eeeeeeeeeeee eee ee eeeeee ee eeeeee ee eeeeeeeeeeeeeee ee 8°M eeeee ee e eeeeeeeeeeeee eeeeeeee ee eeeeeee eeeeeee 88 ee 88% eeeee (Meeeee 88).[‌88‌,‌88‌] Mee eeeeeeee eeeeeeeeee eeeeeeee eeeeeee eeeeeee eeeee eeeeeeeee α-eeeeeeeeee eeeeeeeee, eeeeeeeeee ee eeeee 88, eee eeeeeeeeeeeee. Meeeeeeeeee 88 ee eeee eee e eeeeeeeee ee eeeeeeeeee eeee.

Meeeee 88 Meeeeeeeeeeee ee Meeeee eeee e Meeeee Meeeeeee Meeee[‌88‌]

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

Meeeee 88 [8+8] Meeeeeeeeeeee ee Meeeeeeeeee eeee e Meeeeee[‌88‌]

Meeee ee e eeee eeeee eeee ee eeeeeeeeee eeee eeeeeeeee eee [8+8]-eeeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeeeeee.[‌88‌] Meeee eeeeeeeee eee eeeeeeeee eeeeeeeee ee eeeeeeeeeeee eeeeeeeeee, eee eeee eeee eeee eee eee eeeeeeeeeee ee eeeeeeeeeee eee eeeeeee eeeeeeeeeeee eeeeeeee. Mee eeeeeeeeeee eeeeeee eeee eee eeeee eeeeeeeee eeee ee eeeeee ee eee eeeeeee eeeeeeeeeeee eeeeee ee eeeeeeeee ee eee ee-eeeeeeeeee eeeeee eeeeee eeee ee eeee e eeeeeeeeeeeeeeee eeeeeee ee e eeeeeeee eeeeeeeeeeee. Meeeeeee ee eeee eeeeeeeee eeee ee eeeeeeeee ee eeee eeeeeee.

Meeeeeee ee eeeeeeeeeee-8,8-eeeee ee eeeee eeee-8,8-eeeeeeee [(eeeeeeeeeeeeee)eeeeee] ee eee eeeeeeee ee 88eee% eeeeeeeeeeeeeeeeee ee eeeeeeeee eeeeeee eee 88 eeeee eeeee ee eeeeeeeeeeee 888 ee 88% eeeee (Meeeee 88).[‌88‌] Meeeeee eeeeeeee ee eee eeeeeeeee ee eee eeeeee eeeeeeeee e eeeeeeeeee eeee eeeeeeeee e eeeeee eeee eeeeeeeeeee-8,8-eeeee eeeeeee ee e eeeeeeeeeeeeeeee eeeeee eee eee eeeeeee ee eeeeeeeeeee-8,8-eeeee. Meeeeeeeeeeeeeee eeee eee eeeeeeeee Meeeeee eeeeeeeee, ee eeeeeee eeeeeeee eeeee eeeee eeeeeee. M eeeeee ee eeeeeeeeeeeeeee eeeeee, eeeeeeeeeee ee eee eeeeeeeeeeee ee eeeeeeeeeeeeeeeeee ee eeeeee eeee eee eeeeeeee ee eee eeeeeeeeeeee. Meeeeee, eeee eeeeeeee eee ee eeeeeee ee ee ee eeeeeeeeeeeeeeeeeee eeeeeee eeee ee eeeeeeee ee eee eeeeeeeee.

Meeeee 88 Meeeeeeeeeeee ee Meeee Meee-8,8-eeeeeeee eeee Meeeeeeeeee-8,8-eeeee[‌88‌]

Mee [8+8]-eeeeeeeeeeeee eeeeeeee ee ee ee eeeee eeeeeee ee 8,8-eeeeeeeee. Meeeee eee eeee eeeee eeeeeee e eeeeeeee eeeeeeeee eeeeeeee ee eeeee. (M)-8-Meeeee-8-eeeeeeeeeeeeeeeeeeeeee (888) eeeeee eeee eeee-eeeee eeee-8,8-eeeeeeee (888) ee eee eeeeeeee ee 88eee% eeeeeeeeeeeeeeeee ee eeeeeee ee eeee eeeeeeeeeee ee eeee e eeeeeee ee eeeeeeeeeee eeeeeeeeeeeee 888M eee 888M (88:8) ee 88% eeeee (Meeeee 88).[‌88‌] Mee eeeee eeeeeeeeeeee 888M eee ee eeeeeeeee eeee ()-eeeeeee. Mee Meeeeee eeeeee ee eee eeeeeeeee eeee eeee-eeeee eeee-8,8-eeeeeeee (888) eeeeeeeee e eeeeeeeeee eeee eeee ee eee eeeeeeeee eeeeeeeee eeeee ee eeeeeeeeeeeee 888, eeeeeee ee ee eeeeeee eeee eeee eeee ee eee eeeeeeeeeeeeeeee eeeeeeee. Meeeeeeeeee ee eee eeeeeeeee eeeeeeeee eee eeeeeeeee eeeee. Meeeeee, eeee eeeeeeee eee ee eeeeeee ee ee eeeeee eeeee ee eeeeeeeeee Meeeeee eeeeeeeee. Mee eeeeeeeeeeeeeee ee eee eeeeeee ee eeeeeeeeee eeeeee eee eeeeee Meeeeee eeee.[‌88‌]

Meeeee 88 [8+8] Meeeeeeeeeeee ee ee Meeee eeee eeee-Meeee Meee-8,8-eeeeeeee ee eee Meeeeeeee ee ()-Meeeeee[‌88‌]

Me eeeeeeee eeeeeeeee ee eee eeeeeee eeeee ee eeeeeeeeeee ee Meeeee 88. Mee ee eeeeee, eeeeeeeeee eeeeeeeee 888 ee eee eeeeeeee eeeeeeee eeeee ee e [8+8]-eeeeeeeeeeeee eeeeeeee eeeeeee eeee-eeeee eeeeeeee eee eeeee eeee-8,8-eeeeeeee ee eeee eeeeeeeeeeee 888 ee 88% eeeee eee 88% ee.[‌88‌] Mee eeeee, ee eeee ee eee eeee eeeeeeeee ee eeee eeeeeee eeee eee eeee eeeeeee ee eee eeee ee eeeeeee.

Meeeee 88 Meeeeeeeee Meeeeeeee [8+8] Meeeeeeeeeeee ee eeee-Meeee Meeeeeee eeee Meeee Meee-8,8-eeeeeeee[‌88‌]

Meeeee 88 eeeeeeeeeee ee eeeeeeeeeee ee eeee eeeeeeeeeee ee eee eeeeeeeee ee M-eeeeeeeeeeeeeeeeeeee. Meee eeeeee eeee-8,8-eeeeeeee ee eeeeeee eeee M-eeeeeeeeee 888 ee eee eeeeeeee ee 88eee% eeeeeeeeeeeeeeeeee ee eeeeeee ee eeee eeeeeeeeeee, eeeeeeeeeee ee M-eeeeeeeeeeeeeeeeeee 888 eeeee eeeee ee 88% eeeee.[‌88‌] Mee eeeeeeeee eeeeeee eee eeee eeeeeeee eeee eee eeee eeeeeeeee eeeee. Mee eeeeeeee eeeeeee ee ee eeeeeeeeee ee eeeeee eeee eee eeeeeee eeee eeeeeeee ee eeeeeeee eeeeeeeee. Mee M-eeeee eeeeeeee eee eeeeeee eeeeeeeee eeee eeeeeeee eeeeeee eeeeeeeeeee ee 8-eeeeeeeeeeeeeee eeee.

Meeeee 88 [8+8] Meeeeeeeeeeee ee Meeeee Meee-8,8-eeeeeeee eee e Meeeeeeeee[‌88‌]

References


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