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Intramolecular reactivity of functionalized arylcarbenes: 2-allyloxyphenylcarbenes

โœ Scribed by Frank Gotzhein; Wolfgang Kirmse

Book ID
104256463
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
185 KB
Volume
38
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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 intramolecular addition. Under these conditions, intramolecular reactions and intersystem crossing of triplet 8 proceed at similar rates (kT -kTs).

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