Photochemically Induced Ring Opening of Spirocyclopropyl Oxindoles: Evidence for a Triplet 1,3‐Diradical Intermediate and Deracemization by a Chiral Sensitizer

URN to cite this document:: urn:nbn:de:bvb:355-epub-452525
DOI to cite this document:: 10.5283/epub.45252

Li, Xinyao ; Kutta, Roger J. ; Jandl, Christian ; Bauer, Andreas ; Nuernberger, Patrick

; Bach, Thorsten

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Date of publication of this fulltext: 23 Mar 2021 06:16

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Abstract

The photochemical deracemization of spiro[cyclopropane-1,3 '-indolin]-2 '-ones (spirocyclopropyl oxindoles) was studied. The corresponding 2,2-dichloro compound is configurationally labile upon direct irradiation at lambda=350 nm and upon irradiation at lambda=405 nm in the presence of achiral thioxanthen-9-one as the sensitizer. The triplet 1,3-diradical intermediate generated in the latter ...