Regiodirected substitution of [2.2]paracyclophanedienes and [2.2]paracyclophanes through tricarbonylchronium complexation
✍ Scribed by Michael Stöbbe; Oliver Reiser; Thies Thiemann; Rhys G Daniels; Armin de Meijere
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 273 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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Paracyclophane-1,9-diene (1) is readily deprotonated at upon treatment with zinc(II) chloride in 1,2-dichloroethane to give the indene-annelated [2.2]paracyclophane 9 (72%) and its vinylic positions with BuLi to give the monolithium derivative 2 and -in the presence of TMEDA -even the 1,9-/ the bis(
## Abstract The title compounds 8 and 1 have been synthesized in three steps each from 1,2‐dibromo[2.2]paracyclophan‐1‐ene (2) and 1,2,9,10‐tetrabromo[2.2]paracyclophane‐1,9‐diene (4), respectively. Copper‐mediated coupling of vinyl bromides 2 and 4 with methyl‐ and phenylmagnesium bromide gives su