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. Author manuscript; available in PMC: 2019 Oct 1.
Published in final edited form as: Nat Chem. 2019 Apr 1;11(5):478–487. doi: 10.1038/s41557-019-0233-x

Figure 2. Challenges in designing reactions that deliver stereodefined alkenyl nitriles.

Figure 2

Unlike other types of Mo alkylidenes, such as those that contain a chlorine atom (I), a nitrile-substituted variant (II) is more strongly stabilized due to electronic factors, and is therefore less reactive. The higher polarizability of Mo=C bond of a CN-substituted alkylidene and the alkene of acrylonitrile facilitates reaction via III, generating metallacyclobutane IV and causing nonproductive olefin metathesis. Ar, aryl.