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Please login or sign up for a free trial to access the full content. Variation 2: Nucleophilic Substitution Reactions

DOI: 10.1055/sos-SD-045-00477

Iyoda, M.Science of Synthesis, (201045512.

Reaction of tetrachlorocyclopropene 9 with carbanions 27 produces the corresponding dianions 28, stabilized by a contribution of the charge-separated, symmetric resonance structure 29.[‌35‌] The dianions 28 can be converted into [3]radialenes by electron-transfer oxidation (Scheme 9). A variety of hetero[3]radialenes, such as cyclopropanetrione and its nitrogen, phosphorus, and sulfur counterparts, can be synthesized by nucleophilic substitution reactions.[‌35‌] However, the syntheses of hetero[3]radialenes are not included in this section.

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8-eeeeeee 8. MeMM8M(M)Me, MMM/MMMM; 8. 8; 8. M8 88 [‌88‌]
8-eeeeeee 8. MeMe ee MeMM8M(M)Me, MMM/MMMM; 8. 8; 8. M8 8888 [‌88‌,‌88‌]
8-eeeeeee 8. MeMM8M(M)Me, MMM/MMMM; 8. 8; 8. M8 88 [‌88‌]
8-eeeeeee 8. MMM; 8. 8; 8. M8 88 [‌88‌]

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