Reaction of ethyl 2-haloethyl-1-tetralone-2-carboxylate and samarium diiodide: first example of intramolecular O-alkylation of samarium ketyl radical by carbon–halogen bond

Hasegawa, Eietsu; Iwaya, Kazuki; Iriyama, Takumi; Kitazume, T.; Tomura, Masaaki; Yamashita, Yoshiro

doi:10.1016/s0040-4039(00)01020-0

Cited by 2 publications

(1 citation statement)

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“…The enol form of C then induced a second intramolecular cyclization, i.e. via a nucleophilic addition of the enol oxygen to C α to yield 8 . Complex 6a in acetone was converted to complex 8a within 30 min by a reversible ring-opening process followed by a formal methanol elimination reaction and then the same ring-closing process.…”

Section: Resultsmentioning

confidence: 99%

Tandem Cyclization in Ruthenium Vinylidene Complexes with Two Ester Groups

Chang

Cheng

et al. 2011

Organometallics

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The reaction of [Ru]-Cl ([Ru] = Cp(PPh3)2Ru) with o-ethynyl-substituted methyl benzoate, followed by a sequential deprotonation and electrophilic alkylation reactions by further reacting with base and various alkyl haloacetates, respectively, generated several disubstituted ruthenium vinylidene complexes. In the deprotonation reactions of these disubstituted vinylidene complexes containing two ester groups, tandem cyclizations of the ligand is accompanied with a methanol elimination to generate a new organometallic product containing a three-ring indenofuranone ligand, which structure has been confirmed by a single-crystal X-ray diffraction analysis. Facile protonation and methylation are observed in these indenofuranone complexes. Additionally, for the simple furyl complex containing an O-benzyl group, a 1,3-migration of the benzyl group is observed to yield a lactone product and a Claisen rearrangement is also observed in analogous complexes with O-allyl or O-propargyl groups.

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Section: Resultsmentioning

confidence: 99%