Why is benzyl-gem-diacetate remarkably stable in aqueous solution?

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 SN1 mechanism in aqueous solution to give benzaldehydes as the final product thr...

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Bibliographic Details
Published in:International journal of chemical kinetics 2009-08, Vol.41 (8), p.554-557
Main Authors: Jagannadham, V., Padmavathi, D. Annapurna, Sanjeev, R.
Format: Article
Language:English
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Summary: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 SN1 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
ISSN:0538-8066
1097-4601
DOI:10.1002/kin.20414