(2-Stannylated butadiene) tricarbonyl iron complexes: Practical reagents for the synthesis of 2-acyldienes

Colson, Pierre-Jean; Franck‐Neumann, M.; Sedrati, M.

doi:10.1016/s0040-4039(01)80408-1

Cited by 27 publications

(3 citation statements)

References 14 publications

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“…In 1984, Flecker, Grevels, and Hess reported a much more facile Fe(CO) 3 transfer reagent (η 2 - cis -C 8 H 14 ) 2 Fe(CO) 3 ( 4 ), which was demonstrated to transfer a Fe(CO) 3 unit effectively to a variety of bidentate ligands in common organic solvents at or above −35°C. A number of successful preparations of dieneiron tricarbonyl complexes employing 4 followed in the literature, for example, the preparation of (2-stannylated butadiene)tricarbonyliron and (substituted cyclohexadiene)tricarbonyliron . In order to see if the intermediate 2 could be detected, the reaction of 1 with the mild Fe(CO) 3 transfer reagent 4 was examined; the results are presented herein.…”

Section: Introductionmentioning

confidence: 99%

Ring Opening of (Spiro[2.4]hepta-4,6-diene)tricarbonyliron: A Revisit

Chao

Liu

1998

Organometallics

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Spiro[2.4]hepta-4,6-diene)tricarbonyliron (2) self-converts to the tethered acyl complex (CO) 2 FeC(O)CH 2 CH 2 (η 5 -C 5 H 4 ) (3) when refluxed for 1 h in common organic solvents. The reaction of 2 with an external electrophile (CPh 3 + , H + ) opens the three-membered ring, resulting in the cation (η 5 -C 5 H 4 CH 2 CH 2 R)Fe(CO) 3 + whose structure was determined by spectroscopic methods and confirmed by X-ray analysis of the PPh 3 derivative (η 5 -C 5 H 4 CH 2 -CH 3 )Fe(CO) 2 (PPh 3 ) + . The reaction of 3 with a strong electrophile (CPh 3 + , Me + ) affords the rotationally restricted Fe-(alkoxy)carbene cation (CO) 2 FedC(OR)CH 2 CH 2 (η 5 -C 5 H 4 ) + , which can be converted to the Fe-(anilino)carbene cation (CO) 2 FedC(NHPh)CH 2 CH 2 (η 5 -C 5 H 4 ) + . 146 °C) originating from 4. If brought to reflux for 1 h, compound 2 in solution is fully converted to 3, whose IR ν(CO) stretching bands are shown in Figure 1d. Compound 3 is not soluble in n-hexane or Et 2 O but is soluble in THF and chlorinated solvents.Reactions of 2 with Lewis and Protic Acids. Scheme 1 shows a proposed, intramolecular, ionic rear-

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Section: Introductionmentioning

confidence: 99%

Ring Opening of (Spiro[2.4]hepta-4,6-diene)tricarbonyliron: A Revisit

Chao

Liu

1998

Organometallics

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“…In a ligand exchange reaction with trans -cyclooctene, the labile complex 36 was applied to the synthesis of the corresponding stable complex tricarbonylbis(η 2 - trans -cyclooctene)iron. , Franck-Neumann used Grevels' reagent (36) for the quantitative complexation of 2-trialkylstannylbuta-1,3-dienes to the corresponding tricarbonyliron complexes . An in situ preparation of Grevels' reagent and subsequent transfer of the tricarbonyliron fragment to dienes without isolation has also been described. , …”

Section: Tricarbonylbis(η2-cis-cyclooctene)ironmentioning

confidence: 99%

“…113,114 Franck-Neumann used Grevels' reagent (36) for the quantitative complexation of 2-trialkylstannylbuta-1,3-dienes to the corresponding tricarbonyliron complexes. 115 An in situ preparation of Grevels' reagent and subsequent transfer of the tricarbonyliron fragment to dienes without isolation has also been described. 116,117…”

Section: Tricarbonylbis(η 2 -Cis-cyclooctene)ironmentioning

confidence: 99%