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Intramolecular reactivity of functionalized arylcarbenes: 1-(hydroxymethyl)-9-fluorenylidene

โœ Scribed by Wolfgang Kirmse; Birgit Krzossa


Book ID
104258619
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
179 KB
Volume
39
Category
Article
ISSN
0040-4039

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Intramolecular reactivity of functionali
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2-Allyloxyphenylcarbenes (8) undergo intramolecular addition (~ 9) and (formal) C-H insertion (-~ 11) competitively. Stereochemical labels indicate that 11 and major amounts of 9 arise from triplet 8. The intermolecular O-H insertion of singlet 8 with methanol (neat) is ca. 50 times faster than intr

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1,2-H shift is the only intramolecular reaction of 7-(1-propenyloxy)-l-indanylidenes (8) whereas 7-(2-propenyloxy)-l-indanylidene (13) and 7-(2-butenyloxy)-l-indanylidenes (19) undergo addition to the sidechain C=C bond and 1,2-H shifts competitively. Owing to the small RCR bond angle of 1-indanylid