598-22-1Relevant articles and documents
A mild and efficient reaction for conversion of carboxylic acids into acid bromides with ethyl tribromoacetate/triphenylphosphine under acid-free conditions
Kang, Dong Ho,Joo, Tae Young,Lee, Eun Hwa,Chaysripongkul, Skaydaw,Chavasiri, Warinthorn,Jang, Doo Ok
, p. 5693 - 5696 (2007/10/03)
Acid bromides were prepared efficiently from carboxylic acids with readily available ethyl tribromoacetate and triphenylphosphine at room temperature under neutral conditions. The present process is applicable to the preparation of various acid bromides from aromatic and aliphatic carboxylic acids. Aromatic carboxylic acids were found to be more reactive than aliphatic carboxylic acids under reaction conditions.
Reagents and Synthetic Methods; 14. A Facile Synthesis of Carboxylic Acid Bromides and Esters under Neutral Conditions via Reaction of the Trimethylsilyl Esters with Triphenylphosphine Dibromide
Aizpurua, Jesus Mari,Palomo, Claudio
, p. 684 - 686 (2007/10/02)
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Noncompeting Metastable Losses of Methyl and Ethylene from Gaseous Butanoic Acid Ions due to Isomerization Prior to Methyl Loss
McAdoo, David J.,Hudson, Charles E.
, p. 7710 - 7713 (2007/10/02)
Metastable C4H8O+. ions obtained from butanoic acid and ethyl butanoate undergo considerable γ-hydrogen exchange prior to losing ethylene, but little exchange prior to losing methyl.Therefore the two fragmentations are not directly competing, contrary to the general assumption that all reactions of an ion in the gas phase are competitive.It is concluded that metastable butanoic acid ions which lose methyl isomerize essentially irreversibly to CH3CH2C.HC(OH)2+ and/or CH3CH(C.H2)C(OH)2+ before the γ-methyl becomes exchanged.This accounts for the difference between γ-hydrogen exchange prior to the loss of methyl and ethylene without invoking isolated electronic states, as previously proposed.Butanoic acid ions generated by the McLafferty rearrangement of butanoate esters have a much weaker metastable loss of ethylene than directly ionized butanoic acid.Collisional activation experiments demonstrate that this results from more of the butanoic acid ions derived from ethyl butanoate than from butanoic acid isomerizing prior to collision.Variation in internal energy probably causes this difference in degree of isomerization with the source of the ion.