Further studies on the pyrolytic domino cyclization of stabilized phosphonium ylides bearing an ortho-aminophenyl group
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Four new stabilized phosphonium ylides containing a 2-(benzyl(methyl)amino)phenyl group have been prepared and characterized and are found, upon pyrolysis under gas-phase flow conditions, to lose Ph3PO and benzyl radical to afford new heterocyclic products resulting from domino cyclization of both C- and N-centred radicals. Most products arise from processes of the former type and have quinoline, phenanthridine or ring-fused phenanthridine structures, while in one case a process of the latter type leads to a benzocarbazole product. The X-ray structure of a 2-(methyl(tosyl)amino)phenyl ylide is also reported.
Aitken , R A , Murray , L & Slawin , A M Z 2018 , ' Further studies on the pyrolytic domino cyclization of stabilized phosphonium ylides bearing an ortho-aminophenyl group ' , Molecules , vol. 23 , no. 9 , 2153 . https://doi.org/10.3390/molecules23092153
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DescriptionThe authors thank the EPSRC (UK) for a DTA studentship (Grant No. EP/P501768/1).
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