The Spirodienone Route for the Functionalization of Calixarenes

Biali, Silvio E.

doi:10.1055/s-2003-36212

Cited by 37 publications

(11 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Although direct treatment of 2 4 with 80 did not afford any sulfilimine products, to our pleasure it was a new efficient method for the preparation of novel thiacalix[4]arene monospirodienones 82 . In classical calixarene chemistry similar spirodienone derivatives are very attractive intermediates to prepare varying derivatives by use of the strained spiro structure and the presence of diene, hydroxy, and carbonyl functions …”

Section: 31 Reaction On Bridging Sulfurmentioning

confidence: 99%

Thiacalixarenes

et al. 2006

View full text Add to dashboard Cite

Section: 31 Reaction On Bridging Sulfurmentioning

confidence: 99%

Thiacalixarenes

et al. 2006

View full text Add to dashboard Cite

“…and O -arylation . There are far fewer reported instances of hydroxy group substitution reactions on calix[4]arenes such as 1 by, for example, hydrogen atoms, amino, or sulfhydryl groups …”

Section: Introductionmentioning

confidence: 99%

Narrow-Rim Functionalization of Calix[4]arenes via Sonogashira Coupling Reactions

2005

View full text Add to dashboard Cite

The narrow (or "lower")-rim hydroxyl groups of calixarenes are known to be resistant to substitution/displacement. The Sonogashira coupling reaction with TMSA and phenylacetylene, however, has now been extended to the bistriflate of p-tert-butylcalix[4]arene, previously known to be resistant to Stille, Neigishi, or Suzuki-Miyaura reactions. Under some of the reaction conditions investigated, the previously unknown narrow-rim mono- and diiodo-p-tert-butylcalix[4]arene products were also produced, in addition to the narrow-rim mono- and dialkynyl products. Homocoupling of the narrow-rim monoethynyl-p-tert-butyl-calix[4]arene produced a new narrow-rim rigid butadiyne-linked bis-p-tert-butylcalix[4]arene.

show abstract

“…The calixarenes are presently one of the most useful building blocks for the construction of molecular hosts . Oxidation of p-tert -butylcalix[4]arene ( 1b ) and/or its derivatives may afford, depending on the reaction conditions, calixquinones, spirodienone calixarene derivatives, calixcyclitols, or bicalix[ n ]arenes. , Oxidation reactions leading to calixarene derivatives possessing carbonyl groups connecting the aryl moieties (dubbed by Gutsche as “ketocalixarenes”) 1a were first described in 1985 by Ninagawa . In 1990, Görmar and co-workers reported that the four methylene groups of p-tert -butylcalix[4]arene tetraacetate 1a can be selectively oxidized to carbonyl functionalities to yield 1d . , Basic hydrolysis of the ester groups of 1d afforded the corresponding tetrahydroxy derivative 1e …”

mentioning

confidence: 99%