ChemInform Abstract: Organic Syntheses via Transition Metal Complexes. Part 67. Metathesis of Enamines by Alkynylcarbene Tungsten Complexes. Formation of Aminobenzenes via Pyranylidene Complexes.

Aumann, Rudolf; Roths, Klaus; Laege, M.; Krebs, Bernt

doi:10.1002/chin.199406205

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(2 citation statements)

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“…Initially, when they attempted to prepare different kinds of α,β-unsaturated Fischer carbene complexes, the reaction of hydroxybenzaldehyde 12 with methyl ethoxycarbene complex 11 was found to accidentally yield the benzopyranylidene complex 13 in 82% yield in the presence of Et 3 N (eq. (3)) [27][28][29][30][31][32][33][34][35][36][37][38][39].…”

Section: [3+3] Cyclizationmentioning

confidence: 99%

“…To obtain butadienyl carbene complexes, a Michael-type addition of 4-amino-pent-3-en-ones to alkynylcarbene complex was investigated and found to give rise to a mixture of 1,2-dihydropyridin-2-ylidene complex 16 and pyranylidene complex 17 in dichloromethane in the presence of Et 3 N [28,29], owing to the competing attack of the nitrogen and the oxygen atom on the carbene carbon before a ring closure process (eq. (4)).…”

Section: [3+3] Cyclizationmentioning

confidence: 99%

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Advances in the synthesis and reactivity of 2-pyranylidene carbene complexes

et al. 2010

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Pyranylidene carbene complexes bearing a pyran ring carbene ligand represent a unique kind of organometallic species due to their special structures and reactivity. In this review, we present a comprehensive summary on the synthesis and reactivity of pyranylidene carbene complexes during the past four decades. 2-pyranylidene carbene complexes, synthesis, reactivity Citation:Wang Q F, Zhang W X, Lin C, et al. Advances in the synthesis and reactivity of 2-pyranylidene carbene complexes.Fischer-type carbene complexes are among the most important organometallic compounds, and these have experienced a considerable surge in recent times because of their widespread application in synthetic organic chemistry since the first carbene complex was reported by Fischer and coworkers in 1964 [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. During the course of the development of Fischer-type carbene complexes, unsaturated Fischer carbene complexes, in which unsaturated substituents are attached to the carbene carbon center, occupy an important status owing to their good reactivity in Michael-type reactions, cycloaddition reactions, transmetalation reactions. The strong electron-withdrawing property of the pentacarbonyl metal moiety and the electron-deficient property of the β-position carbon resulting from electron-transfer from the carbene center play a cooperative effect on the versatile reactivity of unsaturated Fischer carbene complexes [2-18]. 2-Pyranylidene metal carbene complexes bearing a pyran ring carbene ligand are a special kind of unsaturated Fischer carbene complex, that has received much less attention probably because of their limitation of the synthetic methodology. Recently, some important progress has been made *Corresponding author (email: zfxi@pku.edu.cn) by the chemical community. Here we give a comprehensive review of the synthesis and reactivity of the 2-pyranylidene metal carbene complex during the past four decades.

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