Competition in the Three‐Component System Triphenylphosphane/Azo Ester/3‐Hydroxy‐Carboxylic Acid: OH  versus  COOH‐Activation | Zendy

Mulzer Johann | Zendy; Brüntrup Gisela | Zendy; Chucholowski Alexander | Zendy

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Competition in the Three‐Component System Triphenylphosphane/Azo Ester/3‐Hydroxy‐Carboxylic Acid: OH versus COOH‐Activation

Author(s) -

Mulzer Johann,

Brüntrup Gisela,

Chucholowski Alexander

Publication year - 1979

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.197906221

Subject(s) - chemistry , steric effects , carboxylic acid , component (thermodynamics) , competition (biology) , medicinal chemistry , polymer chemistry , organic chemistry , stereochemistry , ecology , biology , physics , thermodynamics

The question whether hydroxy carboxylic acid are activated at the OH and/or the COOH group is of considerable importance, e.g. in syntheses of macrolides and peptides. IN the system (1) (PPh 3 + azo ester)/ (2) the extent of reaction at OH and/or COOH depends upon R 1 and R 1 ; Q = ( (3) + (4) )/ (5) can be correlated almost completely with Taft's steric parameter E s .

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