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1 article(s) from Reisenauer, Hans Peter

Intramolecular hydroxycarbene C–H-insertion: The curious case of (o-methoxyphenyl)hydroxycarbene

Dennis Gerbig,
David Ley,
Hans Peter Reisenauer and
Peter R. Schreiner

Beilstein J. Org. Chem. 2010, 6, 1061–1069, doi:10.3762/bjoc.6.121

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Scheme 1: Unimolecular reactivity of hydroxycarbenes under cryogenic conditions: [1,2]H-Tunneling of 1 and 3 (...

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Scheme 2: A selection of heterocarbenes that undergo intramolecular C–H insertions.

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Scheme 3: Attempted generation of 5 and d-5 as well as their corresponding insertion products.

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Scheme 4: Proposed mechanism for the generation of 8 and 9. The [1,2]H-tunneling process apparently cannot co...

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Figure 1: Unmodified matrix IR spectrum (Ar, 11 K) of the pyrolysis (600 °C) of 5. Traces of 9 are indicated ...

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Figure 2: Unmodified matrix IR spectrum (Ar, 11 K) of the pyrolysis (600 °C) of d-5. Traces of 9 are indicate...

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Scheme 5: Decay of the 2,3-dihydrobenzofuran-3-ol molecular radical cation (8^+•).

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Scheme 6: Attempted generation of 12 and the actual pyrolysis product 11.

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Scheme 7: Unanticipated reaction of 6 upon heating in xylenes.

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Scheme 8: Potential energy hypersurface of (o-methoxyphenyl)hydroxycarbene (5) (not drawn to scale; ZPVE incl...

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Scheme 9: Acid-catalyzed generation of 7 by unreacted 6.

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Published 11 Nov 2010

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