Building blocks for phospha[n]pericyclynes

Assema, S.G.A. van; Kraikivskii, Petr B.; Zelinskii, S. N.; Saraev, V. V.; Jong, G. Bas de; Kanter, Frans J. J. de; Schakel, Marius; Slootweg, J. Chris; Lammertsma, Koop

doi:10.1016/j.jorganchem.2007.02.017

Cited by 15 publications

(7 citation statements)

References 57 publications

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“…Scheme2.Synthesis of phosphanediides 3 and bis(trimethylsilyl)phosphineboranes 4. [8]( the valuesofo nly one of two independent molecules are given): P1ÀB1 1.9685(16), P1ÀN1 1.6987 10,P 1 ÀSi112.2853(4), P1ÀSi12 2.2905 5, N1ÀC111.4797 (15),N 1 ÀC141.4763 14, B1ÀH1A 1.113 (19), B1ÀH1B 1.07 2, B1ÀH1C 1.07 2; N1-P1-B1 118.52(6), N1-P1-Si11 107.29 4, N1-P1-Si12 110.41(4),S i11-P1-Si12 111.523 18, B1-P1-Si11 104.89(6),B 1-P1-Si12 104.12 7, P1-N1-C11 125.17 8, P1-N1-C14 118.24(8), C11-N1-C14 116.37 (9). Table 3.…”

Section: Resultsmentioning

confidence: 99%

“…[18] 3a:C 10 H 18 BLi 2 O 2 P, Fw = 225.90, yellow needle, 0.60 0.24 0.09 mm 3 ,m onoclinic, P2 1 /n (no. 14), a = 12.4001 (9), b = 7.2198(7), c = 14.7720(8) , b = 94.983(3) 8, V = 1317.47 (17) 3 , Z = 4, D x = 1.139 gcm À3 , m = 0.19 mm À1 .T he diffraction experiment was performed on aN onius KappaCCD diffractometer with rotating anode and graphite monochromator (l = 0.71073 )a tat emperature of 125(2) Ku pt oar esolution of (sin q/l) max = 0.65 À1 .T he crystal appeared to be twinned with at wofold rotation about hkl = (1,0,-1) as twin operation. Consequently,t wo orientation matrices were used for the integration with the Eval15 software.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…A clear drawback of these primary phosphines is their pyrophoric nature, high sensitivity to oxidation and noxious character, [1c] which requires experienced chemists with dedicated lab facilities to handle these compounds safely [8] . Furthermore, the appealing primary (dialkylamino)phosphines (R 2 NPH 2 ) that are suitable for further functionalization (treatment with HCl provides the corresponding chlorophosphines) [9] are, in addition, thermally labile. For example, iPr 2 NPH 2 decomposes upon attempted isolation [10] …”

Section: Introductionmentioning

confidence: 99%

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Easy Access to Phosphine‐Borane Building Blocks

Jong

Ortega

Lutz

et al. 2020

Chemistry A European J

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In this paper, we highlight the synthesis of av ariety of primary phosphine-boranes (RPH 2 •BH 3)f rom the corresponding dichlorophosphines,s imply by using Li[BH 4 ]a sr eductanta nd providero ft he BH 3 protectingg roup. The methodo ffers facile access not only to alkyl-and arylphosphine-boranes, but also to aminophosphine-boranes (R 2 NPH 2 •BH 3)t hat are convenient buildingb locks but without the protecting BH 3 moiety thermally labile and notoriously difficult to handle.T he borane-protected primary phosphines can be doubly deprotonated using n-butyllithium to provides oluble phosphanediides Li 2 [RP•BH 3 ]o fw hich the phenyl-derivative Li 2 [PhP•BH 3 ]w as structurally characterized in the solid state.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis and Characterizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Easy Access to Phosphine‐Borane Building Blocks

Jong

Ortega

Lutz

et al. 2020

Chemistry A European J

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“…173 phorus(III), for example, P,P-diethynyl-N,N-diisopropylphosphoramidite (220), 174 were used as building blocks for the synthesis of these compounds. Their successive reactions with ethylmagnesium bromide and dichloro(diisopropylamino)phosphine afford tetraphosphine 221 as a mixture of four stereoisomers in a total yield of *9%.…”

Section: Synthesis Of Macrocyclic Polyphosphines and Their Derivativesmentioning

confidence: 99%

Phosphorus-containing macrocyclic compounds: synthesis and properties

Knyazeva¹,

Бурилов²,

Пудовик³

et al. 2013

Russ. Chem. Rev.

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Main trends in the development of methods for Main trends in the development of methods for the synthesis of phosphorus-containing macrocyclic com-the synthesis of phosphorus-containing macrocyclic compounds in the past 15 years are considered. Emphasis is pounds in the past 15 years are considered. Emphasis is given to reactions producing macrocyclic structures with the given to reactions producing macrocyclic structures with the participation of a phosphorus atom and other functional participation of a phosphorus atom and other functional groups involved in organophosphorus molecules and to groups involved in organophosphorus molecules and to modifications of macrocycles by phosphorus compounds modifications of macrocycles by phosphorus compounds in different valence states. Possibilities of the practical in different valence states. Possibilities of the practical application of phosphorus-containing macrocyclic com-application of phosphorus-containing macrocyclic compounds in difference areas of science and engineering are pounds in difference areas of science and engineering are discussed. The bibliography includes 205 references discussed. The bibliography includes 205 references. .

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“…Ethynylphosphines has been of interest because of not only electronic interaction between the phosphanyl group and the π‐electron system of C≡C triple bond but also spacial characteristics derived from the linear acetylene framework. As for homogeneous catalysis, for example, Ochida and Sawamura have employed bulky ethynyl skeletons for developing tertiary phosphines bearing a large cavity (Fig.…”

Section: Introductionmentioning

confidence: 99%

Preparation via Sterically Promoted S_N2′ Substitution and Structural Characteristics of a Mes*‐Substituted Tertiary Ethynylphosphine

Ito

Nanko

Mikami

2014

Heteroatom Chemistry

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The reaction of a sterically encumbered 2‐bromo‐3‐silyloxyphosphapropene [(Z)‐Mes*‐P = C(Br)CH(OSiMe3)Mes; Mes* = 2,4,6‐tBu3C6H2, Mes = 2,4,6‐Me3C6H2] and butyllithium afforded a bulky ethynylphosphine [Mes*P(nBu)C≡CMes] via SN2′ reaction of the alkyllithium and subsequent beta‐elimination of HBr. The orbital‐controlled reaction and prohibition of the halogen–metal exchange would be induced by the steric encumbrance of the mesityl group. Structural characteristics of the novel ethynylphosphine were also discussed in views of steric encumbrance as well as stereochemistry. The remarkable distortion of Mes* aromatic ring was further discussed according to DFT calculations.

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Building blocks for phospha[n]pericyclynes

Cited by 15 publications

References 57 publications

Easy Access to Phosphine‐Borane Building Blocks

Easy Access to Phosphine‐Borane Building Blocks

Phosphorus-containing macrocyclic compounds: synthesis and properties

Preparation via Sterically Promoted S_N2′ Substitution and Structural Characteristics of a Mes*‐Substituted Tertiary Ethynylphosphine

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Building blocks for phospha[n]pericyclynes

Cited by 15 publications

References 57 publications

Easy Access to Phosphine‐Borane Building Blocks

Easy Access to Phosphine‐Borane Building Blocks

Phosphorus-containing macrocyclic compounds: synthesis and properties

Preparation via Sterically Promoted SN2′ Substitution and Structural Characteristics of a Mes*‐Substituted Tertiary Ethynylphosphine

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Product

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Preparation via Sterically Promoted S_N2′ Substitution and Structural Characteristics of a Mes*‐Substituted Tertiary Ethynylphosphine