Stable C-Halogenated Arsaalkenes

Ramdane, Hassan; Ranaivonjatovo, H.; Escudié, J.; Knouzi, Nourredine

doi:10.1021/om960147s

Cited by 16 publications

(10 citation statements)

References 14 publications

(10 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Deuterated solvents (C 6 D 6 and CDCl 3 ) were dried and stored over 4 Å molecular sieves. NMR spectra were reported in parts per million (ppm) and recorded on a Bruker Avance 300 spectrometer at the following frequencies: 1 38 and difluoro(tert-butyl)(2,4,6-triisopropylphenyl)germane (Tip(t-Bu)-GeF 2 ) 12 were prepared according to previously reported procedures.…”

Section: Methodsmentioning

confidence: 99%

“…Selenium Adduct 2: the crystal is made up of a mixture of about 89% of the three-membered ring species 2 and 11% of a fourmembered ring derivative with a Ge−C−Se−Se moiety; C 38…”

Section: Methodsmentioning

confidence: 99%

“…Elemental analyses were performed by the “ Service de Microanalyse de l’Ecole de Chimie de Toulouse ”. C , C -Dibromo(2,4,6-tri- tert -butylphenyl)arsaalkene (Mes*AsCBr 2 ) and difluoro( tert -butyl)(2,4,6-triisopropylphenyl)germane (Tip( t -Bu)GeF 2 ) were prepared according to previously reported procedures.…”

Section: Methodsmentioning

confidence: 99%

“…This derivative was synthesized according to the procedure previously described . To a diethyl ether solution (50 mL) of C , C -dibromo(2,4,6-tri- tert -butylphenyl)arsaalkene (Mes*AsCBr 2 ) (2.46 g, 5 mmol) cooled to −100 °C was added n -butyllithium (1.6 M in hexane; 3.2 mL, 5.10 mmol) dropwise. After the mixture was stirred at the same temperature for 1 h, a solution of difluoro( tert -butyl)(2,4,6-triisopropylphenyl)germane (1.86 g, 5 mmol) in diethyl ether (20 mL) was slowly added over a period of 30 min.…”

Section: Methodsmentioning

confidence: 99%

See 3 more Smart Citations

Versatile 1,2- and 1,3-Dipole Behavior of the 1-Arsa-3-Germaallene Tip(t-Bu)Ge═C═AsMes*: Formation of a Heterocyclic Arsa(germa)carbene (AsGeHC)

Ghereg

Sotiropoulos²,

Escudié

et al. 2012

Organometallics

Self Cite

View full text Add to dashboard Cite

The 1-arsa-3-germaallene Tip(t-Bu)GeCAsMes* (1; Tip = 2,4,6-triisopropylphenyl, Mes* = 2,4,6-tri-tert-butylphenyl) reacts with selenium, fluorenone, N-tert-butylphenylnitrone, and 9,10-phenanthrenequinone as a 1,2-dipole by the GeC double bond, to give the corresponding three-, four-, five-, and six-membered-ring derivatives 2–5, respectively. Both [2 + 2] and [2 + 4] cycloadditions involving the GeC double bond are observed between 1 and benzil, leading to the four- and six-membered-ring derivatives 6 and 7. In great contrast, 1 reacts with diphenylketene as a 1,3-dipole by the whole GeCAs unit to afford the transient heterocyclic arsa(germa)carbene 12 according to a [3 + 2] cycloaddition. DFT calculations were carried out to understand this particular behavior. This first heavier analogue of an NHC with an arsenic atom rearranges to the tricyclic compound 11.

show abstract

Section: Methodsmentioning

confidence: 99%

“…Selenium Adduct 2: the crystal is made up of a mixture of about 89% of the three-membered ring species 2 and 11% of a fourmembered ring derivative with a Ge−C−Se−Se moiety; C 38…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Versatile 1,2- and 1,3-Dipole Behavior of the 1-Arsa-3-Germaallene Tip(t-Bu)Ge═C═AsMes*: Formation of a Heterocyclic Arsa(germa)carbene (AsGeHC)

Ghereg

Sotiropoulos²,

Escudié

et al. 2012

Organometallics

Self Cite

View full text Add to dashboard Cite

show abstract

“…On the other hand, halogenated derivatives, because of their expected potential for the preparation of functionalised representatives, are of considerable interest [72].…”

Section: Fluoroarsaalkenesmentioning

confidence: 99%

The chemistry of fluorine containing phosphaalkenes, arsaalkenes and selenocarbonyls

Grobe¹,

Van²

2004

Journal of Fluorine Chemistry

View full text Add to dashboard Cite

Isolierung eines anellierten 1,4‐Distibabenzol‐Diradikaloids

et al. 2023

View full text Add to dashboard Cite

Die erste 1,4-Distabenzol-1,4-diid-Verbindung [(ADC)Sb] 2 (5) auf der Basis eines anionischen Dicarbens (ADC) (ADC = PhC{N(Dipp)C} 2 , Dipp = 2,6-iPr 2 C 6 H 3 ) wird als bordeauxroter Feststoff berichtet. Verbindung 5, die einen zentralen sechsgliedrigen C 4 Sb 2 -Ring mit formalen Sb I -Atomen aufweist, kann als ein Basen-stabilisiertes cyclisches Bis-Stibiniden betrachtet werden, in dem jedes der Sb-Atome zwei freie Elektronenpaare trägt. 5 geht eine 2e-Oxidation mit Ph 3 C[B(C 6 F 5 ) 4 ] ein und bildet [(ADC)Sb] 2 [B(C 6 F 5 ) 4 ] 2 (6) als ziegelroten Feststoff. Jedes der Sb-Atome von 6 hat ein ungepaartes Elektron und ein freies Elektronenpaar. Die offenschalige Singulett-Diradikal-Lösung (broken-symmetry) für ( 6) 2 + ist um 2.13 kcal mol À 1 stabiler als die geschlossenschalige Singulett-Lösung. Der diradikalische Charakter von (6) 2 + beträgt nach SS-CASSCF (state-specific complete active space self-consistent field) und UHF (unrestricted Hartree-Fock) 39 % bzw. 36 %. Die Behandlung von 6 mit (PhE) 2 ergibt [(ADC)Sb(EPh)] 2 [B(C 6 F 5 ) 4 ] 2 (7-E) (E = S oder Se). Die Reaktion von 5 mit (cod)Mo(CO) 4 führt zu [(ADC)Sb] 2 Mo(CO) 4 (8).

show abstract

Stable C-Halogenated Arsaalkenes

Cited by 16 publications

References 14 publications

Versatile 1,2- and 1,3-Dipole Behavior of the 1-Arsa-3-Germaallene Tip(t-Bu)Ge═C═AsMes*: Formation of a Heterocyclic Arsa(germa)carbene (AsGeHC)

Versatile 1,2- and 1,3-Dipole Behavior of the 1-Arsa-3-Germaallene Tip(t-Bu)Ge═C═AsMes*: Formation of a Heterocyclic Arsa(germa)carbene (AsGeHC)

The chemistry of fluorine containing phosphaalkenes, arsaalkenes and selenocarbonyls

Isolierung eines anellierten 1,4‐Distibabenzol‐Diradikaloids

Contact Info

Product

Resources

About