C O M M U N I C A T I O N S
Figure 3. CID spectra for m/z 135 ion derived from (a) reaction of 2 with
NO, and (b) deprotonation of 4-hydroxyimino-1-cyclohexenecarbonitrile.
and 4-hydroxyimino-1-cyclohexenecarbonitrile (PDF). This material is
References
Figure 2. Likely products with m/z 135 resulting from the reaction of 2,5-
dicyano-1,5-hexadiene radical anion with NO. Products from both the cyclic
2b and the acyclic 2a structures are considered. A complete list of possible
products resulting from NO addition and direct HCN loss from 2a and 2b
is provided in the Supporting Information.
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The cyclization of the radical anion of 2,5-dicyano-1,5-hexadiene
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Acknowledgment. This work was funded by the National
Science Foundation (CHE-0137627). Thanks also go to the donors
of the Petroleum Research Fund, as administered by the American
Chemical Society, for partial support of this work.
Supporting Information Available: Structures of possible products
formed by addition of NO and direct loss of HCN, table of reactivity
for 2, a list of CID products for the m/z 135 ion and 7, and synthesis
procedures for 2,5-dicyano-1,5-hexadiene, 2,6-dicyano-1,6-heptadiene,
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