CCL: Dihydroxyl compound

[Amiram Goldblum <amiram[A]vms.huji.ac.il>]

 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