Reduction of Epoxides

Murai, S.; Murai, Toshiaki; Katō, Shinzi

doi:10.1016/b978-0-08-052349-1.00249-3

Cited by 18 publications

(10 citation statements)

References 137 publications

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“…Additionally, (Me 3 SiO) 3 SiCH 2 CH 2 CH 2 Cl (7) was used as one of the primary alkyl chlorides. The presumed products can be new types of precursors of amines bearing an oxygen-permeable functional group (35,36). The reaction of the thioamide dianion (2a) with (7) also proceeded smoothly to give the desired product in 98% yield.…”

Section: Resultsmentioning

confidence: 96%

Silylation and alkylation of thioamide dianions ofN-arylmethyl secondary thioamides, and reduction of the resulting thioamides leading to secondary and primary amines

Murai

Michigami

Yamaguchi

et al. 2009

Journal of Sulfur Chemistry

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This paper is dedicated to Professor Juzo Nakayama on the occasion of his 65th birthday and retirement.N -arylmethyl aromatic thioamides were reacted with n-BuLi (2 equivalents), and then treated with silylpropyl chloride and silyl chlorides. As a result, these electrophiles were introduced to the carbon atom adjacent to the nitrogen atom of thioamides via thioamide dianions. The efficiency of the reaction was largely influenced by the substituents on the aromatic ring of thioamides. The reaction of thioamides having pyridyl groups was not always successful and depended on the position of the nitrogen atom of these groups. Reduction of the resulting thioamides with LiAlH 4 proceeded smoothly to give the corresponding secondary N -1-silylarylmethyl amines in good yields. In contrast, the reduction of thioamides bearing pyridyl groups gave complex mixtures. In these cases, the use of DIBAH successfully gave the desired secondary amines.

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Section: Resultsmentioning

confidence: 96%

Silylation and alkylation of thioamide dianions ofN-arylmethyl secondary thioamides, and reduction of the resulting thioamides leading to secondary and primary amines

Murai

Michigami

Yamaguchi

et al. 2009

Journal of Sulfur Chemistry

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“…This was anticipated to provide a base-induced method to deoxygenate epoxides [43], which in the case of deuteration would provide a regiospecific and potentially stereoselective entry to 1-deuterated terminal alkenes [44–45]. Use of a slightly higher molecular weight epoxide, 1,2-epoxydodecane ( 13 ) to facilitate product isolation, gave dodecene ( 14 ) (41%, 50% D [46]) after reaction with CD 3 OD (Scheme 6), where the deuterium incorporation was nonstereoselective [44].…”

Section: Resultsmentioning

confidence: 99%

Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine

Hodgson

Persaud²

2012

Beilstein J. Org. Chem.

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SummaryTerminal epoxides undergo lithium 2,2,6,6-tetramethylpiperidide-induced α-lithiation and subsequent interception with Ph3P to provide a new and direct entry to β-lithiooxyphosphonium ylides. The intermediacy of such an ylide is demonstrated by representative alkene-forming reactions with chloromethyl pivalate, benzaldehyde and CD3OD, giving a Z-allylic pivalate, a conjugated E-allylic alcohol and a partially deuterated terminal alkene, respectively, in modest yields.

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“…On the other hand, the dependence of the torque pulsation on radial and angular components of the flux error has been analyzed in [9] and it was stated that the torque pulsation is more affected by the angular error than the radial error. The angular errors can be reduced by distributing more zero-vector states on the locus of I# so that the rotating speed becomes smoother and angular error approaches zero.…”

Section: Staircase Pulse-width Modulation Principlementioning

confidence: 99%

Analysis of high‐frequency PWM techniques suitable for resonant inverters

Neacșu¹,

Alexa²

1996

Int Trans Elec Energy Syst

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Special Pulse-Width-Modulation ( P WM) techniques capable of realizing true P WM operation of quasi-resonant DC-link inverters are presented. These techniques provide an increased value of the lowest switching time f o r higher carrierfrequencies. The harmonic performances are extensively studied by simulation in comparison with conventional Space-Vector Modulation and a simple algorithm f o r real-time implementation is developed.

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Reduction of Epoxides

Cited by 18 publications

References 137 publications

Silylation and alkylation of thioamide dianions ofN-arylmethyl secondary thioamides, and reduction of the resulting thioamides leading to secondary and primary amines

Silylation and alkylation of thioamide dianions ofN-arylmethyl secondary thioamides, and reduction of the resulting thioamides leading to secondary and primary amines

Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine

Analysis of high‐frequency PWM techniques suitable for resonant inverters

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