The Meerwein Reaction in Amino Acid Synthesis. I. α-Bromo-o-, m-, and p-Chlorohydrocinnamic Acids and the Corresponding Chlorophenylalanines; α-Bromo- and α-Chlorohydrocinnamamide

Cleland, George H.

doi:10.1021/jo01067a082

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The Arylation Reaction1

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Cited by 23 publications

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“…Scheme 1 shows the preparation of the reagent. Aminobenzophenone (3) was diazotized, and acrylic acid and cuprous bromide were added to achieve a Meerwein arylation (Cleland, 1961(Cleland, ,1971Rondestvedt, 1976;Doyle et al, 1977). The resulting (a-bromobenzoyl)hydrocinnamic acid was isolated and then dehydrobrominated.…”

Section: Resultsmentioning

confidence: 99%

Tethered Benzophenone Reagents for the Synthesis of Photoactivatable Ligands

et al. 1995

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A new radiolabeled, bifunctional photoaffinity cross-linking reagent, N-succinimidyl p-benzoyl-[2,3-3H2]dihydrocinnamate, has been synthesized in high yield and with high specific activity. This reagent can be used to append the benzophenone photophore to amino groups of small molecules, such as O-aminoalkylinositol polyphosphates and polypeptides. The resulting tritiated photoaffinity labels can be purified and manipulated in ambient light and can be activated at 360 nm.

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Section: Resultsmentioning

confidence: 99%

Tethered Benzophenone Reagents for the Synthesis of Photoactivatable Ligands

et al. 1995

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“…The Nature of X I t seems to make little difference whether X is C1 or Br. Cleland (7) has employed bromo compounds in the reactions he has examined, but with the exception of C6F6N2+Br-, we have worked with the chloro compounds.…”

Section: The Arylation Reactionmentioning

confidence: 99%