JOURNAL ARTICLE
RESEARCH SUPPORT, N.I.H., EXTRAMURAL
RESEARCH SUPPORT, NON-U.S. GOV'T
RESEARCH SUPPORT, U.S. GOV'T, NON-P.H.S.
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(2+1)-Cycloaddition Reactions Give Further Evidence of the Nitrenium-like Character of 1-Aza-2-azoniaallene Salts.

Cationic 1-aza-2-azoniaallene salts react with structurally constrained alkenes in intramolecular reactions by C-H insertion at the allylic position, or by (2+1)-cycloaddition with the alkene followed by ring opening. The latter reaction gives further evidence of the nitrenium-like character of 1-aza-2-azoniaallene salts. DFT calculations show that alkene addition is intrinsically more favorable, but that predistortion can lead to C-H insertion.

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