From owner-chemistry@ccl.net Wed May 10 15:42:01 2006
From: "Amiram Goldblum amiram]^[vms.huji.ac.il" <owner-chemistry[]server.ccl.net>
To: CCL
Subject: CCL: Dihydroxyl compound
Message-Id: <-31739-060510141618-20017-8q6PEwwI/YYSVc51x9NtTQ[]server.ccl.net>
X-Original-From: Amiram Goldblum <amiram[A]vms.huji.ac.il>
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Date: Wed, 10 May 2006 19:15:30 +0100
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Sent to CCL by: Amiram Goldblum [amiram[*]vms.huji.ac.il]


Hi Kevin,

Compounds with two hydroxyls on the same carbon
are known as "gem diols" and are actually hydrates
of ketones or carbonyls. They are very unstable unless you have
strong electron attractors on the neighboring carbon/s,
such as difluoromethylene and others. With some electron
attractors you may stabilize the ketone ===== hydrate equilibrium
to the hydrate side up to 90%.

Gem diols are supposed to be close to tetrahedral intermediates in the attack
on amide carbonyls by water. They have been interesting as potential
inhibitors of aspartic proteinases and other enzymes.


With kind regards,

Amiram