“…An insoluble black, oligomeric material and antimony mirrors on the walls of the flask were slowly formed under these conditions. As already observed for primary vinyl- and alkynylstibines, compounds 5 and 6 are more stable than the corresponding arsenic derivatives. , 2 …”
Section: Resultssupporting
confidence: 54%
“…All chemicals were used without further purification. Tributylstannane, allenyltributylstannane, vinyltributylstannane, allenylphosphine ( 1 ), allenylarsine ( 3 ), and divinylarsine ( 4 ) were prepared as previously reported.…”
The base-induced rearrangement of divinylphosphine led to the corresponding 3-phospha-1,3-pentadiene, which is sufficiently stable to be detected at
room temperature by 31P NMR spectroscopy. This
diene
was trapped by addition of 2-propanethiol to the reaction
mixture. Under similar conditions, the transient
1-phospha-1,3-butadiene and 3-arsa-1,3-pentadiene were chemically trapped. Divinylstibine and allenylstibine, both
new compounds and potential precursors of stibadienes,
were also prepared.
“…An insoluble black, oligomeric material and antimony mirrors on the walls of the flask were slowly formed under these conditions. As already observed for primary vinyl- and alkynylstibines, compounds 5 and 6 are more stable than the corresponding arsenic derivatives. , 2 …”
Section: Resultssupporting
confidence: 54%
“…All chemicals were used without further purification. Tributylstannane, allenyltributylstannane, vinyltributylstannane, allenylphosphine ( 1 ), allenylarsine ( 3 ), and divinylarsine ( 4 ) were prepared as previously reported.…”
The base-induced rearrangement of divinylphosphine led to the corresponding 3-phospha-1,3-pentadiene, which is sufficiently stable to be detected at
room temperature by 31P NMR spectroscopy. This
diene
was trapped by addition of 2-propanethiol to the reaction
mixture. Under similar conditions, the transient
1-phospha-1,3-butadiene and 3-arsa-1,3-pentadiene were chemically trapped. Divinylstibine and allenylstibine, both
new compounds and potential precursors of stibadienes,
were also prepared.
“…Even for arsenic or tin, it is only quite recently that the corresponding derivatives have been synthesized. [5][6][7][8] On the other hand, the high reactivity of other heterocomAbstract: The gas-phase acidity of CH 3 ÀCH 2 XH (X = S, Se, Te), CH 2 =CHXH (X = S, Se, Te) and PhXH (X = S, Se) compounds was measured by means of Fourier transform ion cyclotron resonance mass spectrometry. To analyze the role that unsaturation plays on the intrinsic acidity of these systems, a parallel theoretical study, in the framework of the G2 and the G2-(MP2) theories, was carried out for all ethyl, ethenyl (vinyl), ethynyl, and phenyl O-, S-, Se-, and Te-containing derivatives.…”
The gas-phase acidity of CH3-CH2XH (X=S, Se, Te), CH2=CHXH (X=S, Se, Te) and PhXH (X=S, Se) compounds was measured by means of Fourier transform ion cyclotron resonance mass spectrometry. To analyze the role that unsaturation plays on the intrinsic acidity of these systems, a parallel theoretical study, in the framework of the G2 and the G2(MP2) theories, was carried out for all ethyl, ethenyl (vinyl), ethynyl, and phenyl O-, S-, Se-, and Te-containing derivatives. Unsaturated compounds are stronger acids than their saturated analogues, because of the strong pi-electron donor ability of the heteroatoms that contributes to a large stabilization of the unsaturated anions. Ethynyl derivatives are stronger acids than vinyl compounds, while phenyl derivatives have an intrinsic acidity intermediate between that of the corresponding vinyl and ethynyl analogues. The CH2=CHXH vinyl compounds (enol-like) behave systematically as slightly stronger acids than their CH3-C(H)X (keto-like) tautomers. Vinyl derivatives are stronger acids than ethyl compounds, because the anion stabilization attributable to unsaturation is greater than that undergone in the neutral compounds. Conversely, the enhanced acidity of the ethynyl derivatives with respect to the vinyl compounds is due to two concomitant effects, the stabilization of the anion and the destabilization of the neutral compound. The acidities of ethyl, vinyl, and ethynyl derivatives containing heteroatoms of Groups 14, 15, and 16 of the periodic table are closely related, and reflect the differences in electronegativity of the CH3CH2-, CH2=CH-, and CH[triple chemical bond]C- groups.
“…This molecule has been only recently synthesized and characterized by NMR and infrared low-resolution (2) spectroscopies, photoelectron spectroscopy (3), and mass spectrometry (2,4). ␣-unsaturated arsines are the precursors of the corresponding carbon-arsenic multiple-bond derivatives (3,5) and they present, among the primary arsines, particular properties due to the presence of hydrogens and an unsaturated substituent on the same arsenic atom (3,4).…”
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