TY - JOUR
T1 - Hydrolysis of 1,4,6-Trioxaspiro[4.5]decanes to δ-Lactones Using 2,3-Dichloro-5,6-dicyanobenzoquinone in Aqueous Acetone
AU - Vasudevan, Sundar
AU - Watt, David S.
PY - 1994/1/1
Y1 - 1994/1/1
N2 - A selective hydrolysis of 1,4,6-trioxaspiro[4.5] decane orthoesters by 2,3-dichloro-5,6-dicyanoquinone (DDQ) in aqueous acetone in the presence of other acid-sensitive ketals is suggested to involve the formation of a charge-transfer complex followed by hydrolysis. A hydride-transfer mechanism for this oxidation was excluded.
AB - A selective hydrolysis of 1,4,6-trioxaspiro[4.5] decane orthoesters by 2,3-dichloro-5,6-dicyanoquinone (DDQ) in aqueous acetone in the presence of other acid-sensitive ketals is suggested to involve the formation of a charge-transfer complex followed by hydrolysis. A hydride-transfer mechanism for this oxidation was excluded.
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U2 - 10.1021/jo00081a013
DO - 10.1021/jo00081a013
M3 - Article
AN - SCOPUS:0028354828
SN - 0022-3263
VL - 59
SP - 361
EP - 364
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -