3-Isothiazolone-cis-3-Thiocyanoacrylamide Equilibria<sup>1,2</sup>

Crow, WD; Leonard, Nelson J.

doi:10.1021/jo01019a037

Cited by 64 publications

(22 citation statements)

References 1 publication

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“…The yields refer to analytically pure compounds and are not optimized. 1 H, 13 C, 19 F, and 31 P NMR spectra were recorded on a Jeol JNX 400, a Varian Inova 400, or a Bruker Avance 400 spectrometer at ambient temperature. Chemical shifts are reported relative to the residual solvent peaks or tetramethylsilane ( 1 H, 13 20 were synthesized according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of the First Stable Palladium Allenylidene Complexes

et al. 2008

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Oxidative addition of BrCtCC(dO)NR 2 to [Pd(PPh 3) 4 ] affords the trans-alkynylbromopalladium complexes trans-[Br(PPh 3) 2 Pd-CtCC(dO)NR 2 ] (NR 2) NMe 2 (2a), N(CH 2) 4) (2b)). Subsequent reaction of 2a,b with P i Pr 3 in excess gives trans-[Br(P i Pr 3) 2 Pd-CtCC(dO)NR 2 ] (5a,b). The analogous reaction of 2b with P(C 6 H 4 OMe-4) 3 gives trans-[Br(P{C 6 H 4 OMe-4} 3) 2 Pd-CtCC(dO)NR 2 ] (7b), and that of 2a with trifluoroacetate gives trans-[(F 3 CCOO)(PPh 3) 2 Pd-CtCC(dO)NMe 2 ] (9a). Methylation of 2a,b, 7b, and 9a with either MeOTf or [Me 3 O]BF 4 and ethylation of 2a,b with [Et 3 O]BF 4 yield the first cationic allenylidene complexes of palladium, trans-[R*(PR′ 3) 2 Pd-CtCC(OMe)NR 2 ] + X-(R*) Br, CF 3 COO; R′) Ph, C 6 H 4 OMe-4, i Pr; X) OTf, BF 4).

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Section: Methodsmentioning

confidence: 99%

Synthesis of the First Stable Palladium Allenylidene Complexes

et al. 2008

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“…Elemental analysis: Heraeus CHN-O-Rapid. Complexes 1a, 1b and 10 [23], propynoic acid dimethylamide [31], and 3-methylimino-3-phenyl-propyne [32] were prepared according to literature procedures. All other chemicals were commercial products and used as supplied.…”

Section: Generalmentioning

confidence: 99%

A convenient route to six-membered heterocyclic carbene complexes: Reactions of aminoallenylidene complexes with 1,3-bidentate nucleophiles

Szesni

Drexler

Weibert

et al. 2005

Journal of Organometallic Chemistry

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“…Elemental analysis: Heraeus CHN-O-Rapid. The following alkynes were prepared according to literature procedures: Propynoic acid dimethylamide [27], 1-pyrrolidin-1-yl-propynone [28], propynoic acid diphenylamide [29], methyl(1-phenyl-prop-2-ynylidene)amine [30].…”

Section: Generalmentioning

confidence: 99%

A new method for the preparation of N-stabilized allenylidene complexes of chromium and tungsten

Fischer¹,

Szesni²,

Roth³

et al. 2003

Journal of Organometallic Chemistry

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Displacement of tetrahydrofuran in [(CO) 5 M(THF)] (M 0/Cr, W) by the anion [C Å/C Ã/C(Ä/X)Y] ((X 0/O; NR; Y 0/NR ? 2 , Ph) followed by alkylation of the resulting metalate with [R ƒ 3 O]BF 4 (R ƒ0/Me, Et) offers a convenient and versatile route to p-donorsubstituted allenylidene complexes, [(CO) 5 M Ä/C Ä/C Ä/C(XR ƒ)Y]. Allenylidene complexes in which the terminal carbon atom of the allenylidene ligand constitutes part of a heterocycle are likewise accessible by this reaction sequence. Reaction of [(CO) 5 M(THF)] with Li[C Å/C Ã/C(Ä/NMe)Ph] (and subsequent protonation of the metalate afford [(CO) 5 M Ä/C Ä/C Ä/C(NMeH)Ph] in high yield. As indicated by the spectroscopic data of the compounds and the X-ray analyses of three representative examples, these allenylidene complexes are best described as hybrids of allenylidene and zwitterionic alkynyl complexes with delocalisation of the electron pair at nitrogen towards the metal center. Dimethylamine reacts with the amino(phenyl)allenylidene complex [(CO) 5 Cr Ä/C Ä/C Ä/ C(NMe 2)Ph] (7a) by addition of the amine across the C a Ä/C b bond to give selectively the E-alkenyl(amino)carbene complex [(CO) 5 Cr Ä/C(NMe 2) Ã/CH Ä/C(NMe 2)Ph] (12). In contrast, the reaction of dimethylamine with the amino(methoxy)allenylidene complex [(CO) 5 Cr Ä/C Ä/C Ä/C(NMe 2)OMe] (1a) proceeds by addition of the amine to the C g atom and subsequent elimination of methanol to give the substitution product [(CO) 5 Cr Ä/C Ä/C Ä/C(NMe 2) 2 ] (13). Triphenylphosphane neither adds to the C a nor the C g atom of 7a but upon irradiation displaces a CO ligand to form a cis-allenylidene(tetracarbonyl)phosphane complex 15.

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3-Isothiazolone-cis-3-Thiocyanoacrylamide Equilibria^1,2

Cited by 64 publications

References 1 publication

Synthesis of the First Stable Palladium Allenylidene Complexes

Synthesis of the First Stable Palladium Allenylidene Complexes

A convenient route to six-membered heterocyclic carbene complexes: Reactions of aminoallenylidene complexes with 1,3-bidentate nucleophiles

A new method for the preparation of N-stabilized allenylidene complexes of chromium and tungsten

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3-Isothiazolone-cis-3-Thiocyanoacrylamide Equilibria1,2

Cited by 64 publications

References 1 publication

Synthesis of the First Stable Palladium Allenylidene Complexes

Synthesis of the First Stable Palladium Allenylidene Complexes

A convenient route to six-membered heterocyclic carbene complexes: Reactions of aminoallenylidene complexes with 1,3-bidentate nucleophiles

A new method for the preparation of N-stabilized allenylidene complexes of chromium and tungsten

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3-Isothiazolone-cis-3-Thiocyanoacrylamide Equilibria^1,2