From: Harry J. Elston <helston**At_Symbol_Here**midwestchemsafety.com>
Subject: Re: [DCHAS-L] The Safety Zone: [New post] Hydrocyanation without using hydrogen cyanide
Date: Tue, 23 Feb 2016 06:57:35 -0600
Reply-To: DCHAS-L <DCHAS-L**At_Symbol_Here**MED.CORNELL.EDU>
Message-ID: CAJ2hcffaySDAwaxngued6UvhVwhLhDnwyV+c95PkVU21Sn02xg**At_Symbol_Here**mail.gmail.com
In-Reply-To
Demystify:
Good morning, Alan:
I think the point of the post is that the process risk is reduced by the removal of HCN as a reagent in the hydrocyanation reaction. Nitriles, as a class of compounds still present cyanide hazard if improperly handled.
Xianjie Fang, Peng Yu, and Bill Morandi of the Max Planck Institute for Coal Research use a nickel catalyst as a shuttle to pluck hydrogen and a cyano group from a donor nitrile and transfer them to an alkene to form a nitrile. The team shows the reaction is useful to make aryl nitriles and for functionalizing biomolecules such as tyrosine and estrone.
In addition, the transfer hydrocyanation is made reversible on demand by selecting starting reagents that control the thermodynamic equilibrium of the reaction-the nitriles can be reverted to complementary alkenes. The team uses this retrohydrocyanation to make styrene, terpene, and aliphatic alkene derivatives from nitriles.
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