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

Article abstract of DOI:10.1016/S0040-4039(97)00091-9

1,2-H shift is the only intramolecular reaction of 7-(1-propenyloxy)-1-indanylidenes (8) whereas 7-(2-propenyloxy)-1-indanylidene (13) and 7-(2-butenyloxy)-1-indanylidenes (19) undergo addition to the side-chain 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 triplet-sensitized photolysis (k(TS) > k(T)).