The mechanism of 1,4-addition of dibromomethylene

Lambert, Joseph B.; Ziemnicka-Merchant, Barbara T.

doi:10.1021/jo00298a017

J. Org. Chem.

1990

DOI: 10.1021/jo00298a017

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The mechanism of 1,4-addition of dibromomethylene

Joseph B. Lambert¹,

Barbara T. Ziemnicka-Merchant²

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Cited by 11 publications

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“…1,4-Addition of DMC to 2 is sufficient to explain the formation of 6 and 1,4-addition of carbenes to conjugated systems is precedented, although DMC itself gave such a product, after rearrangement, in only one case …”

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confidence: 99%

Reactions of Dimethoxycarbene with Dimethyl 2,3-Dicycanomaleate and Fumarate

and

Warkentin

2007

Org. Lett.

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Dimethoxycarbene, in 2-fold or larger excess, reacts with dimethyl 2,3-dicyanomaleate and fumarate to afford an unstable dihydrofuran 1:1 adduct that was shown to react further with the carbene to afford a 2:1 adduct reported previously. In an astonishing process, the dihydrofuran reacts with water to afford a mixture of (d,l and meso) dimethyl 2,3-dicyanosuccinates in which both hydrogen atoms of water were used to hydrogenate a C=C bond.

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confidence: 99%

Reactions of Dimethoxycarbene with Dimethyl 2,3-Dicycanomaleate and Fumarate

and

Warkentin

2007

Org. Lett.

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“…12 In light of the good solubility of tetrabutylammonium fluoride in this solvent, its ability to bring about the exhaustive dehydrobromination of representative vicinal dibromides has been probed as summarized in Table 1. 9,[13][14][15][16][17] All of the cited yields relate to isolated products with purities above 97%. The scale of the reported reactions ranged from 50-500 mg of dibromide.…”

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confidence: 99%

Tetrabutylammonium Fluoride in Dimethyl Sulfoxide: A Reagent Combination for the Twofold Dehydrobromination of Vicinal Dibromides

Dura¹,

Paquette²

2006

Synthesis

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Eine ungewöhnliche Addition von 1,2‐Alkadienyliden‐Carbenen an 1,3‐Diene; 1,4‐Addition an starre und flexible 1,3‐Diene

et al. 1991

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wandlung von H,C=CHR in HC=CHR (R = iPr, Ph) in einem einkernigen Rheniumkomplex mit tBuOK als Base haben Gladysz und Mitarbeiter kiirzlich berichtetIL41, wobei vermutlich die positive Ladung am Metallzentrum fur den Reaktionsverlauf entscheidend ist. A rhcitsvorschrIften 8: Eine Suspension von 121 mg (0.15 mmol) 6[15] in lOmL iPrOH wird mit 500 mg (4.72 mmol) Na,CO, und 0.4 mL (3.17 mmol) H,C=CHrBu versetzt und 3 h auf 75' C erwarmt. Nach dem Abkuhlen wird das Solvens entfernt. der Ruckstand init 25 mL Pentan extrahiert und der Extrakt im Vakuum zur Trockne eingeengt. Das verbleibende rotbrdune81 wird in 4 mL Hexan gelost und die Losung iiber AI,O, (neutral, Aktivitatsstufe V. Siulenhohe 20 cm) chromatogrdphiert. Mit Hcxan wird zuerst eine ordngefarbene und danach eine gelbe Fraktion eluiert. Von letzterer wird das Solvens ahgezogen und der Riickstand aus 2 mL Pentan bei -78 C umkristallisiert. Man erhilt gelbe. kurzzeitig luftatabile Krislalle; Ausbeule 30 mg (30%); Pp = 154°C (Zers.). Korrekte Elementaranalyse. 10: Herstellung analog 8. ausgehend von 9[8]. in Ethanol; rote Kristalle; Ausheute 59%; Fp = 159 C (Zers ). Korrekte Elementaranalyse. Eingegangen am 22. Mirz 1991 [Z 45211 _ _ _ _~ [I] a) P. 0. Stoutland. R. G. Bergman, J Am. Chem. Soc. 107 (1985) 4581; b) J. Silvestre, M. J. Calhorda, R. Hoffmann, P. 0. Stoutland, R. G . Bergman, Ur~un~nietallic.rS(1986) 1841. c ) P. 0. Stoutland, R. G. Bergman, J Am. Chem. Soc. 110 (1988) 5732. Fur umgekehrte Reihenfolge der thermo-~~ ~

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The mechanism of 1,4-addition of dibromomethylene

Cited by 11 publications

References 1 publication

Reactions of Dimethoxycarbene with Dimethyl 2,3-Dicycanomaleate and Fumarate

Reactions of Dimethoxycarbene with Dimethyl 2,3-Dicycanomaleate and Fumarate

Tetrabutylammonium Fluoride in Dimethyl Sulfoxide: A Reagent Combination for the Twofold Dehydrobromination of Vicinal Dibromides

Eine ungewöhnliche Addition von 1,2‐Alkadienyliden‐Carbenen an 1,3‐Diene; 1,4‐Addition an starre und flexible 1,3‐Diene

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The mechanism of 1,4-addition of dibromomethylene

Cited by 11 publications

References 1 publication

Reactions of Dimethoxycarbene with Dimethyl 2,3-Dicycanomaleate and Fumarate

Reactions of Dimethoxycarbene with Dimethyl 2,3-Dicycanomaleate and Fumarate

Tetrabutylammonium Fluoride in Dimethyl Sulfoxide: A Reagent Combination­ for the Twofold Dehydrobromination of Vicinal Dibromides

Eine ungewöhnliche Addition von 1,2‐Alkadienyliden‐Carbenen an 1,3‐Diene; 1,4‐Addition an starre und flexible 1,3‐Diene

Contact Info

Product

Resources

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Tetrabutylammonium Fluoride in Dimethyl Sulfoxide: A Reagent Combination for the Twofold Dehydrobromination of Vicinal Dibromides