A new synthesis of substituted vinylsilanes and vinyl iodides

Huynh, Chanh; Linstrumelle, G.

doi:10.1016/s0040-4039(01)87195-1

Cited by 46 publications

(10 citation statements)

References 14 publications

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“…The IR spectra of all but the last sample indicated that the product of interaction was the a form of 4. The IR spectrum of the last sample taken after 22 h showed that product mixture was mostly the ß form of 4 (about 95%) with a small amount of the ammonium salt of o-acetamidobenzoic acid (about 5%).…”

mentioning

confidence: 99%

Silanes in organic synthesis. 8. Preparation of vinylsilanes from ketones and their regiospecific cyclopentenone annulation

Paquette¹,

Fristad²,

Dime³

et al. 1980

J. Org. Chem.

142

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fraction (ft) of unconverted 1 at time t was determined from the IR spectra by using the ratio of the intensity of the absorption band at 5.7 µ , which is due to the carbonyl band for 1, to the intensity of the absorption band at 6.2 µ , which is an aromatic band found in all samples and, consequently, remains relatively constant. The decrease in ft as a function of t is first order as shown in Figure 1, from which was deduced that the half-life of 1 under these conditions is about 90 h.The NMR spectra of the samples, removed after 8,76, and 296 h, showed that the components of the mixture were 1, 5, and 4 and that the corresponding ratio changed from 90:9:1 after 8 h to 6:3:1 after 76 h to 2:9:9 after 296 h. (b) With NH3 Vapor Saturated with H20 To Give 4 (Expt 15). Experiment 14 was repeated with the modification that air was metered into the system after it was bubbled through concentrated aqueous NH4OH (i.e., 30% NH3). Samples were removed after 1.5, 3, 5, 6.5, and 22 h. The data (Figure 1) show 100% conversion to 5 showing that little or no side products are formed in the conversion.

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confidence: 99%

Silanes in organic synthesis. 8. Preparation of vinylsilanes from ketones and their regiospecific cyclopentenone annulation

Paquette¹,

Fristad²,

Dime³

et al. 1980

J. Org. Chem.

142

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“…As an example, we have reported earlier that vinylphosphane 5 (PEt 2 instead of PPh 2 ) underwent P oxidation and protodesilylation concomitantly when kept in aqueous acetone for several days [10]. In an effort to achieve an iododesilylation at the vinylsilane moiety, we allowed 4a, d, e to react with iodine chloride at rt and quenched the reaction with aqueous sodium thiosulfate (Scheme 3) [17][18][19][20]. Instead of the expected addition product or vinyl iodide, though, desilylated 3-diphenylphosphoryl-acrylamides 7a, d, e were isolated in almost quantitative yields after work-up.…”

Section: Synthesesmentioning

confidence: 99%

Phospha-Michael reaction of tertiary phosphanes Ph₂P–X (X=SiMe₃, Cl) and N-triflyl-propiolamides

Fiore

Maas

2019

Zeitschrift Für Naturforschung B

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The uncatalyzed silylphosphanylation of acetylenic N-trifluoromethylsulfonyl-carboxamides by Ph2P–SiMe3, formally an insertion of a C,C triple bond into a P–Si bond, is reported. Some characteristic functional group transformations of the resulting 3-PPh2-2-SiMe3-N-triflyl-acrylamides were briefly explored: transamidation of the N-triflylamide group with allylamine, P oxidation and protodesilylation. A hydrophosphorylation of the acetylenic triple bond with chloro(diphenyl)phosphane is also reported.

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“…5, 11 Under copper(I) catalysis, (2) reacts with conjugated enones in a 1,4-fashion (eq 13), 11,12 and the diorganocuprate derived from (2) behaves in a similar fashion (eq 14). 13 …”

Section: Tmsmentioning

confidence: 99%

(2-Bromovinyl)trimethylsilane

Cunico

2001

Encyclopedia of Reagents for Organic Synthesis

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A new synthesis of substituted vinylsilanes and vinyl iodides

Cited by 46 publications

References 14 publications

Silanes in organic synthesis. 8. Preparation of vinylsilanes from ketones and their regiospecific cyclopentenone annulation

Silanes in organic synthesis. 8. Preparation of vinylsilanes from ketones and their regiospecific cyclopentenone annulation

Phospha-Michael reaction of tertiary phosphanes Ph₂P–X (X=SiMe₃, Cl) and N-triflyl-propiolamides

(2-Bromovinyl)trimethylsilane

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A new synthesis of substituted vinylsilanes and vinyl iodides

Cited by 46 publications

References 14 publications

Silanes in organic synthesis. 8. Preparation of vinylsilanes from ketones and their regiospecific cyclopentenone annulation

Silanes in organic synthesis. 8. Preparation of vinylsilanes from ketones and their regiospecific cyclopentenone annulation

Phospha-Michael reaction of tertiary phosphanes Ph2P–X (X=SiMe3, Cl) and N-triflyl-propiolamides

(2-Bromovinyl)trimethylsilane

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Phospha-Michael reaction of tertiary phosphanes Ph₂P–X (X=SiMe₃, Cl) and N-triflyl-propiolamides