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Intramolecular reactivity of functionalized arylcarbenes: 7-alkenyloxy-1-indanylidenes

โœ Scribed by Frank Gotzhein; Wolfgan Kirmse

Book ID
104256464
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
199 KB
Volume
38
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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-indanylidenes, the intramolecular chemistry is dominated by the singlet state even if the carbenes are generated by tripletsensitized photolysis (krs > kT).

๐Ÿ“œ SIMILAR VOLUMES

Intramolecular reactivity of functionali
Intramolecular reactivity of functionalized arylcarbenes: 2-allyloxyphenylcarbenes
โœ Frank Gotzhein; Wolfgang Kirmse ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 185 KB

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