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Novel protecting groups. III. A study of the reaction of 2‐picolyl 1‐oxide derivatives with acetic anhydride
Author(s) -
Ikeda Kazuyoshi,
Tsuchida Kiyomi,
Monma Taeko,
Mizuno Yoshihisa
Publication year - 1974
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570110310
Subject(s) - chemistry , acetic anhydride , hydrolysis , pummerer rearrangement , oxide , phosphate , organic chemistry , medicinal chemistry , nuclear chemistry , polymer chemistry , catalysis
Abstract 2‐Picolyl 1‐oxides (I‐VIII) were prepared and the reaction of I‐VII with acetic anhydride was followed by the gas chromatography. In this reaction, the increasing order of the rate of disappearance of the 2‐pieolyl 1‐oxide derivatives was found to be IV>III>VII>I>VI>II>V. Under comparable conditions, a half‐life of VIII is midway between that of I and VI. The 2‐picolyl 1‐oxide group was found to be potentially useful for the blocking of hydroxyl functions of phosphates ( viz. , VIII), although ca. 4% of the organic phosphate remained unblocked after the deblocking procedure (acetic anhydride treatment and subsequent hydrolysis).