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Why is benzyl‐ gem ‐diacetate remarkably stable in aqueous solution?
Author(s) -
Jagannadham V.,
Padmavathi D. Annapurna,
Sanjeev R.
Publication year - 2009
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.20414
Subject(s) - chemistry , solvolysis , carbocation , aqueous solution , cleavage (geology) , medicinal chemistry , organic chemistry , hydrolysis , geotechnical engineering , fracture (geology) , engineering
Benzyl‐ gem ‐diacetate is synthesized and performed its solvolysis in water at 25°C. It did not solvolize even for a year, whereas its counterparts benzyl‐ gem ‐diazide and dihalides underwent spontaneous cleavage through a S N 1 mechanism in aqueous solution to give benzaldehydes as the final product through α‐azido benzyl and α‐halo benzyl carbocation intermediates, respectively. The possible explanations are offered for the extraordinary stability of the benzyl‐ gem ‐diacetate in water. © 2009 Wiley Periodicals, Inc. Int J Chem Kinet 41: 554–557, 2009