Journal of the American Chemical Society
COMMUNICATION
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(11) One of the major byproducts from cis-9b was identified as a
cyclopropanated material derived from a putative carbenoid such as 13.
The 1H and 13C NMR signals of this material were identical to those of
the cyclopropanated product of cis-9b catalyzed by the cationic gold
complex used in Table 1. In addition, MALDI mass spectroscopy
analysis of the products derived from both cis- and trans-9b showed
clusters of high molecular masses ranging from 300 up to 1233, implying
the formation of oligomers associated with platinum metal.
(12) The formation of at least three inseparable byproducts pre-
cluded the unambiguous identification of their structures.
(13) The terminal alkynyl-substituted substrate corresponding to 9j
generated a complex product mixture. The expected allene product was
identified in the NMR spectrum but was too unstable to be isolated via
purification on silica gel.
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dx.doi.org/10.1021/ja204979r |J. Am. Chem. Soc. 2011, 133, 12964–12967