TY - JOUR
T1 - Hydroxide Ion‐Initiated Deuteration of Very Weak CH Acidsunder Phase Transfer Catalysis Conditions
AU - Halpern, Marc
AU - Feldman, David
AU - Sasson, Yoel
AU - Rabinovitz, Mordecai
PY - 1984/1
Y1 - 1984/1
N2 - The deuteration of organic compounds with pKa values of up to ca. 34 has been achieved by a special type of phase transfer catalysis. As is well known, hydroxide ions can be extracted into an organic phase from aqueous sodium hydroxide in the presence of quaternary ammonium salts. It has now been shown that these extracted hydroxide ions are more basic than the hydroxide ions at the interface. Exploiting this observation, diphenylmethane, 10,11‐dihydrodibenzo[a,d]cycloheptene and xanthene (pKa = 34, 31, and 27, respectively) could be deuterated quantitatively.
AB - The deuteration of organic compounds with pKa values of up to ca. 34 has been achieved by a special type of phase transfer catalysis. As is well known, hydroxide ions can be extracted into an organic phase from aqueous sodium hydroxide in the presence of quaternary ammonium salts. It has now been shown that these extracted hydroxide ions are more basic than the hydroxide ions at the interface. Exploiting this observation, diphenylmethane, 10,11‐dihydrodibenzo[a,d]cycloheptene and xanthene (pKa = 34, 31, and 27, respectively) could be deuterated quantitatively.
UR - http://www.scopus.com/inward/record.url?scp=84943855058&partnerID=8YFLogxK
U2 - 10.1002/anie.198400541
DO - 10.1002/anie.198400541
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AN - SCOPUS:84943855058
SN - 0570-0833
VL - 23
SP - 54
EP - 55
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 1
ER -