Thank you, Dr. Hall, for that reminder. These short articles by our brilliant colleagues serve as souvenirs that I collect on my safety journey. And I relish
the comments by you and others on this discussion list. These all allow me to better serve my employees, coworkers, and the public in general. I always look forward to what you, Dr. Elston, Monona, and the others have to say on these various topics.
Mark Ellison
From: DCHAS-L Discussion List [mailto:dchas-l**At_Symbol_Here**med.cornell.edu]
On Behalf Of Alan Hall
Sent: Tuesday, February 23, 2016 6:26 AM
To: DCHAS-L**At_Symbol_Here**MED.CORNELL.EDU
Subject: Re: [DCHAS-L] The Safety Zone: [New post] Hydrocyanation without using hydrogen cyanide
I'll remind the group that all nitriles are cyanogens, either from spontaneous decomposition or by hepatic enzyme activity.
Borron SW: Cyanogenic Aliphatic Nitriles, in: Hall AH, Isom GE, Rockwood GA (eds),Toxicology of Cyanides: Experimental, Applied andCclinical Aspects,Wiley Blackwell, 2015,pp. 1666-180.
On Tue, Feb 23, 2016 at 5:57 AM, Secretary, ACS Division of Chemical Health and Safety <secretary**At_Symbol_Here**dchas.org> wrote:
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New post on The Safety Zone
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From this week's C&EN, a
method to conduct hydrocyanation without using hydrogen cyanide and--bonus!--with reversibility:
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.
The paper is in Science, DOI:
10.1126/science.aae0427.
Credit: C&EN
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