An Efficient One-Pot Synthesis of 1,4-Diacyl-2,3,5,6-tetramethoxybenzenes via Biscuprated Precursors

Bringmann, Gerhard; Geuder, Torsten; Harmsen, Sven

doi:10.1055/s-1994-25658

Cited by 4 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The bismetalation with n BuLi followed by treatment with acid chlorides or Weinreb amides did not afford the desired products. Finally, the reaction between 3,6-biscuprates of 13 , prepared by bismetalation and subsequent treatment with CuI, and acid chlorides according to Bringmann was crowned with success. The reduction of the keto groups could be smoothly accomblished with HSiEt 3 /CF 3 COOH reagent .…”

Section: Resultsmentioning

confidence: 99%

Nanoscale Molecular Rods with a New Building Block for Solubility Enhancement

Wessig

Möllnitz

2008

J. Org. Chem.

View full text Add to dashboard Cite

A new building block bearing a [1,3]dioxolo[4,5- f][1,3]benzodioxole core was developed to enhance the solubility of molecular rods by lateral alkyl chains. On incorporation in molecular rods with oligospiroketal structure, the straight geometry is retained, which was concluded from the X-ray crystal structure analysis of one of the rods. The determination of the solubility of a collection of rods bearing this building block revealed that already a butyl group efficiently hinders the aggregation of the rods and consequently causes a considerable enhancement of the solubility. Piperidine rings are located at the ends of the rods, which offer the opportunity for versatile functionalization. Thus, an N, N'-bis(azidoacetyl)-functionalized rod was prepared, which could serve as rigid linkage, initiated by a "Click" reaction.

show abstract

Section: Resultsmentioning

confidence: 99%