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35.1.1.9.2.4 Variation 4: [2+2]-Cycloaddition Reactions

DOI: 10.1055/sos-SD-035-00121

Ulrich, H.Science of Synthesis, (200735120.

Some chlorocumulenes or chloroheterocumulenes, generated in situ, undergo cyclodimerization reactions to give chlorocyclobutanes. For example, trichloroallene 13, generated from 1,2,3,3-tetrachloroprop-1-ene with sodium amide in liquid ammonia at 75°C gives a mixture of the two isomeric [2+2] cycloadducts 14 and 15 in quantitative yield (Scheme 7).[‌19‌] However, it should be emphasized that undiluted trichloroallene explodes on standing at room temperature, therefore due caution should be exercised when handling this reagent. Several chloroallene dimers are listed in Table 1.

Meeeee 8 Meeeeeeeeeeeeeeee ee Meeeeeeeeeeeeee[‌88‌]

Meeee 8 Meeeeeeeeeee Meeeee[‌88‌‌88‌]

M8 M8 M8 M8 Meee (°M) Meeee (88/88) Meeeee (%) ee 88+88 Mee
Me M M M 88 88:88 88 [‌88‌]
Me MM8Me M M 88 888:8 e.e. [‌88‌]
Me Me Me MM8Me ee 888:8 888 [‌88‌]
Me Me Me Me ee 888:8 88 [‌88‌]
Me Me Me M 88 8:8 e.e. [‌88‌]
Me Me Me M ee 8:888 88 [‌88‌]
8-MeM8M8 8-MeM8M8 Me M 8 8:888 88 [‌88‌]
MMMMM MMMMM Me MMM ee 8:888 88 [‌88‌]

e e.e.=eee eeeeeeee.

Mee eeeeeeeee ee eeeeeeeeeeeee eeee eeeeeee eeeeeeee eeeeeeeeeeee eeeeeeeee eee eeeeeeeeeeeeeeee ee eee eeeeeeee (eee MeeeeeMeee, Mee.M 88/8, e8888). Meeeeee, eeeee eeeeeeeeeee eeeeeee eeee eeeeeeeeeeeee eee eeeee eeeeeee eee eeeeeeee ee eeeeeeee eee eeee eeeeeeee eeeeee eeeeeeeeee eeee eeeeeeeeeeeee ee eeeeeee. Me eeee eeeeee eee eeeee eeeeeeeeee 88, eeeeeee eeee eeeeeeeeeeeeeeeeeee eeeeeeee (88) eee 8-eeeeeeeeeeeeeee eeeeeeee (88) ee eeeeeeee ee 88% eeeee (Meeeee 8).[‌88‌]

Meeeee 8 Meeee Meeeeeeeeee ee Meeeeeeeeeeee eee Meeeeee[‌88‌]

Meeeeeeee, eeeeeeeeeee eeeeeee eeee eeeeee(eeeeee)eeeeee eee eeeeeeeeeeeee (88% eeeee), ee eeeeee(eeeee)eeeeee eee eeeeeeeeeeeee (88% eeeee) eee eeeeeeee.[‌88‌]

Meeeeeeeeeeee eeee eeeeeee [8+8]-eeeeeeeeeeeee eeeeeeeee ee eeeeeee eee eeeeee ee eeeeeeeeee. Me eeeeeee ee eee eeeeeeee ee eeeeeeeeeeee 88, eeeee eee eeeeeeeee eeee eeeeeeeeeeee eeeeeeee eee eeeeeeeeeeeee ee eeeeee, eeee eeeeeeeeeeeeeee 88, eeeee eeeee e 88.8:88.8 eeeeeeeeeee eeeeeee ee eee-88, eee eeee-88 (Meeeee 8).[‌88‌] Mee eeeee ee eee eeeeeeee 88 eeeeeee ee eee eeeeeee eeee ee eee eeeeeeee (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeeeeeeee ee Meeeeeeeeeee ee Meeeeeeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeee 8

Meeeeee Meeee (eee-88/eeee-88) Mee
eeeeee 8:8.8 [‌88‌]
Me8M 8:8.8 [‌88‌]
MMMe8 8:8.8 [‌88‌]
MeMM 8.8:8 [‌88‌]

M eeeeeee [8+8] eeeeeeeeeee ee eeeeeeee eeee eeeeeeeeeeeee eee eeeeee(eeeeeeeee)eeeeee, eeeeee ee eee eeeee (8%).[‌88‌] Mee eeeeeeeeeeeee eeeeeeee ee eeeeee(eeeeee)eeeeee eeee eeeeeeeeeeeeeeeeeeee eeeeeee eeeee[8.8]eeeeeeeeee.[‌88‌] Mee eeeeeeee ee eeeeeeeeeeee, eeeeeeeee eeee eeeeeeeeeeeeee eeeeeeee eee eeee, ee eeeeeeeeeeeeeeeeee ee eeeeeee eeeee ee eeee eeeeeeeeeee eee 88 eeeee eeeeeee e 88% eeeee ee eee [8+8] eeeeeeeeeee.[‌88‌]

Meeeeeeeeeeee eeee eeeeeee eeeeeeeeeeeeee [8+8]-eeeeeeeeeeeee eeeeeeeee eeee eeeeeeee eeeeeeeeeee eeeeee eeeeeee. Mee eeeeeeeeeeeee 88 eee eeeeeeeee eeee eee eeeeeeeeeeeee eeee eeeeeeee eeeeeeeee 88 eee eeeeeeeeeeeee ee eeee eee 8-eeeeeeeeeeeee[8.8.8]eeeeee-8-eee (88) ee 88% eeeee. (Meeeee 88).[‌8‌]

Meeeee 88 Meeeeeeeeeeeee Meeeeeeeeeeee Meeeeeee ee ee α-Meeeeeeeeeee eeee ee Meeeee Meeeee[‌8‌]

Meeeeeee eeeeeeeeeeeee eee eeee ee eeeeeeeee eeee 8,8-eeeeeeee eeee eeeeeeeee eee eeee eeee ee eeeeeeeee eeeeeeeeeeeeeee ee eeee eee eeeeeeee eeeeeeeeeeee ee eeee eeeeee.[‌88‌]

Meeee eeeeee eeee eeeeeee eee eeeeeeeeeeeee eeeeeeee eeee eeeeeeeeeeeee. Mee eeeeeee, eeee eeeeeeeeeeee (88) eee eeeeee(eeeeee)eeeeee (88), eee [8+8] eeeeeeeeeee 88 ee eeeeeeee ee 88% eeeee. Mee eeeeee eeeeeee 88 ee eeee eeeeee ee 88% eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeee ee Meeeee(eeeeee)eeeeee ee Meeeeeeeeeee[‌88‌]

Meeeeeee, eeeeeeeeeeee (88), eeeeeeeee ee eeee eeee eeeeeeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeee eeee, eeeeee eeee eee eeeee eeeeeeeeeee 88 (M8=Me) ee eeeeee eee eee-eeeeeeeeeee 88 (M8=Me) ee 88% eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeee ee Meeeeeeeeeee ee Meeee Meeeeeeeeeee[‌88‌]

Meee eeeee eeeeeeeeeee 88 (M8=Me) ee eeee ee eeee eeeeeeee eeeeeeeeeee 88 (M8=Me) ee eeeeeeee ee 88% eeeee. Meeee eeeeee ee eee eeeeeeeeeeee eee eeeeeeee eeee eeeee eeeeeeeeeee eeeeeeeeeee eeeeeee eee-eeeeeeee eeeee. Meee eeeeeeeeeeee ee eeeeeeeee eeeee eeeee eeeeeeeeee ee eeeee eeeeeeeeeeeee ee eeeeeee eeeee, ee eeeeeeeeeeee eee eeeeeeee.

Meeee eee eeeeeeee ee eeeeeeeeeeeeee eee 8,8-eeeeeeeeeeeeeee eeeeeeeeeee eeeee eee eeeeee [8+8] eeeeeeeeeee, 8,8-eeeeeeee-8,8-eeeeeeeee-8,8-eeeeeeeeeeeeeeeeeeeee ee ee 88% eeeee, eee eeeeeeeee eeeeeeee eeeeeee eeeeee(eeeeee)eeeeee eee 8,8-eeeeeeeeeeeeee eeeee eeee eee eeeeee 8-eeeeee-8,8-eeeeeeeeeeee-8-ee-8-eee eeeeeee. Mee eeeeeee eeeeeeeeeee eeeee eeeeeee ee eee eeeeeeee ee eeeeeee eeeeeeeeeeeee.[‌88‌]

Meeeeee, eeeeeeee, eeee ee 88, eeeee eeee eeeeeeeeeeee (88) ee eeee eee [8+8] eeeeeeeeeee 88 ee 88% eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeee ee Meeeeeeeeeee ee Meeeeeee[‌88‌]

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

Meeeee 88 Meeeeeeeeeeee ee Meeeee(eeeeee)eeeeee ee Meeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeeee eeeeeeeee e [8+8]-eeeeeeeeeeeee eeeeeeee eeeeee eee M=M eeee ee eeeeeeeeeeeeeeeeeeeee ee eeee eee- eee eeeee-eeeeee-8-eee eeeeeeeeeee ee eeeeeeeeeeeee eeeee eeeeeee.[‌88‌]

Meeeeeeeeeeee eee eeee eeeeeee [8+8]-eeeeeeeeeeeee eeeeeeeee ee M=M-eeeeee eeeeeeeeee, eeee ee eeeeeeeeeee ee eeeeeeeeeeeee ee eeee β-eeeeeee. Meeeeeee ee eee eeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeee ee e eeeeeee ee eeeeeeeeeee 88 eee eeeeee ee Meeee 8. Me eeee eeeeeeee eeeeeeeeeeee (88), eeeee eee eeeeeeeee ee eeee eeee eeeeeeeeeeee eeeeeeee, eee eee eeeeeeeeee eee eeeeeee ee eeeee ee eee eeeeeeee ee eeeeeeeeeeeee ee 8888°M ee eeeeeeeee eeeeee. M eeeeeee ee eee-eee eeeee-eeeeeee ee eee β-eeeeee 88 ee eeeeeeee ee eeeeee eeeeee.

Meeee 8 Meeeeeeeeee ee β-Meeeeee ee eee Meeeeeeeeeeee ee Meeeeeeeeeee ee Meeeeeeeeee[‌88‌‌88‌]

M8 M8 Meeeee (eee-88/eeeee-88) Meeee (%) Mee
Me Me e.e. 88 [‌88‌]
Me 8-Mee 8:888 88 [‌88‌]
Me 8-MeMM8M8 8:888 88 [‌88‌]
Me 8-MeM8M8 88:88 88 [‌88‌]
8-Mee Me e.e. 88 [‌88‌]
8-MeMM8M8 8-Mee 8:8 88 [‌88‌]
8-MeMM8M8 8-MeMM8M8 8:888 88 [‌88‌]
8-MeMM8M8 8-MeM8M8 88:88 88 [‌88‌]
8-MeMM8M8 8-M8MM8M8 8:8 88 [‌88‌]
8-MeMM8M8 8:8 88 [‌88‌]
8-M8MM8M8MM8 8-MeM8M8 e.e. 88 [‌88‌]

e e.e.=eee eeeeeeee.

Mee eeeeeeeeeeeeee ee eeeeee(eeeee)eeeeee (88), eeeee eee eeeeeeeee ee eee eeeeeeeeeee ee 8-eeeee-8-eeeeee-8-eeeeeeeeeeee-8(8M)-eee ee eeeeeee, ee eeeeeeeeeeee ee eeeeeeeeeeeeeeee 88 eeeeee β-eeeeeee 88 ee eeeeee ee eeee eeeeee (eee Meeee 8).[‌88‌] Mee eeeeeeee ee eeeeee eeeeeeeeeeeeeee ee eeee eee eeeee eeeee ee eeeeee eeeee ee eee eeeeeeee ee 88.

Meeee 8 Meeeeeeeeee ee β-Meeeeee ee eee Meeeeeeeeeeee ee Meeeee(eeeee)eeeeee ee Meeeeeeeeeee ee Meeeeeeeeeeeeeee[‌88‌]

M8 M8 M Meeee (%) Mee
Me Me M 88 [‌88‌]
Me Me M 88 [‌88‌]
Me Me M 88 [‌88‌]
Me eMe M 88 [‌88‌]
Me Me M 88 [‌88‌]
Me e-Me M 88 [‌88‌]
Me Me M 88 [‌88‌]
Me Me M 88 [‌88‌]
Me Me M 88 [‌88‌]
Me eMe M 88 [‌88‌]
Me Me M 88 [‌88‌]
Me e-Me M 88 [‌88‌]
Me Me M 88 [‌88‌]

Meee eeeeeeeeeeee ee eeeee ee eeeeeeeeeeeeeeeeeeeeeee, eee [8+8] eeeeeeeeeee ee eeeeeeee ee 88% eeeee.[‌88‌] Meeeeeee, eeeeee(eeeeee)eeeeee eee eeeeee(eeeeee)eeeeee eeeee eeee eeeeeeeeeeeeeeeeeeeeeeee ee eeee eee [8+8] eeeeeeeeeeee ee 88 eee 88% eeeee, eeeeeeeeeeee.[‌88‌] Mee eeeeeeeeeeeee eee eeeeeeeee ee eeeeeeeeeeeeeeeeeee ee eee eeeeeeeeeeeee eeee eeeeeeeee eeee eeeeeeeeeeeee ee eeeeeeeee eeeeee.

Meeeeeeeeeee Meeeeeeee

Meeeeee (8-Meeeee-8-eeeeee-8-eeeeeeeeee[8.8.8]eeeeee)eeeeeeeeeee (88, M8=Me):[‌88‌]

MMMMMMM: Meeeeeeeeeee eeeeeeee ee e eeeeeeeeeee eee ee eeeeeeeee eee eeeeeeeeee ee eee eeee, eeee, eee eeeeeeeeeee eeeeee.

Me e eeeeeee eeeeeeeeee ee eeeeeeeee Me (8.8e, 88.8eeee),[‌88‌] ee eeeee Me8M (88eM) eeeee M8 eee eeeee eeeeeeeeeeee eeeeeeee (8.8e, 8.88eeee) eee 88 (M8=Me; 8.88e, 8.88eeee). Mee eeeeeee eee eeeeeee ee ee eee 8e. Meeee eeeeeeeeee ee eee Me, e eee. ee MeMMM8 eeee eee eeeee ee eeeeeeeeeee eee MeMe8. Mee Me8M eeeeeee eee eeeeeeeeee, eee eeeeee eeeeeeeeeeeeee eeee eeeeeee eee 8.88e (88%) ee eeeeeeeee 88; eeeee: 8.88e (88%).

References


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