Synthesis of Cyclopropane Derivatives. Precursors for Dimethylenecyclopropane and Trimethylenecyclopropane

Blomquist, A. T.; Longone, Daniel T.

doi:10.1021/ja01517a056

Cited by 42 publications

(12 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Also, in contrast to other MCPs derivatives Feist's acid dimethyl ester does not undergo peracid oxidation 11. An anomalous frequency shift was observed for hydrogen out‐of‐plane deformations of the methylene group in IR spectra of Feist's acid derivatives (ν C=CH2 = 10.8–11.1 μ) as compared to parent MCP and unconjugated olefins (ν C=CH2 is about 11.25 μ) 12. 1,3‐Dipolar cycloaddition of phenyl azide to dimethyl ester of Feist's acid leads to formation of 1‐phenyl‐4‐[1,2‐bis(methoxycarbonyl)ethyl]‐1,2,3‐triazole as consequence of the unusual rearrangement of an intermediate triazoline cycloadduct 13.…”

Section: Introductionmentioning

confidence: 86%

“…IR spectra were measured as 2 % solutions in CHCl 3 or CCl 4 . Starting materials were prepared according to literature data: Feist's acid,12 diethyl ester of Feist's acid,12 dimethyl ester of Feist's acid was prepared by reaction of Feist's acid with Me 2 SO 4 in Et 2 O at room temperature, C ‐aryl‐ N ‐phenylnitrones 6c – f ,22 C ‐aryl‐ N ‐methylnitrones 6a , b 23…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Esters of Feist's Acid: Some Insights into the Electronic Structure and Reactivity of Methylenecyclopropanes Ring‐Substituted with Acceptor Groups

2009

View full text Add to dashboard Cite

Keywords: Cycloaddition / Electronic structure / Methylenecyclopropane / Nitrone / Substituent effects 1,3-Dipolar cycloaddition of C-aryl-N-aryl-or N-methylnitrones with esters of Feist's acid (3-methylenecyclopropanetrans-1,2-dicarboxylic acid) occurs with the formation of the corresponding spiro[cyclopropane-1,4-isoxazolidine] cycloadducts as single isomer with yields in the range of 17-59 %. The reaction proceeds with inverse regiochemical outcome compared to cycloadditions with unsubstituted methylenecyclopropane. Feist's esters are significantly less active towards cycloaddition with nitrones than methylenecyclopropane and reactions require prolonged heating at elevated temperature. The electronic structures of Feist's esters were investigated by means of molecular photoelectron spectroscopy and theoretical calculations (HF/6-31G*, B3LYP/6-

show abstract

Section: Introductionmentioning

confidence: 86%

Section: Methodsmentioning

confidence: 99%

Esters of Feist's Acid: Some Insights into the Electronic Structure and Reactivity of Methylenecyclopropanes Ring‐Substituted with Acceptor Groups

2009

View full text Add to dashboard Cite

show abstract

“…After epoxidation of 163 with MCP-BA, oxaspiropentane 164 was reacted with catalytic lithium iodide 42 at 0 °C for 5 min to produce 165 in excellent yield (Scheme 26). The well-known Feist's acid 16643 could be used as an ideal starting material; resolution of this diacid had been reported by Doering and Roth 44. Following the literature, the racemic Feist's acid was resolved as its quinine salt by recrystallization from EtOH, yielding optically pure (+)-167 in good yield.…”

mentioning

confidence: 97%

Syntheses of Oxetanocin A and Related Unusual Nucleosides with Bis(hydroxymethyl)-branched Sugars

Ichikawa¹,

Kato²

2004

Synthesis

View full text Add to dashboard Cite

Since the naturally occurring unusual nucleoside oxetanocin A and its derivatives have been found to be effective as anti-HIV-1 and anti-herpes virus agents in 1986, the syntheses of different types of sugar-modified nucleoside analogs have been reported. In this review we will give an overview of the efforts to synthesize oxetanocin A from the first synthesis in 1987 and the related unusual nucleosides with bis(hydroxymethyl)-branched sugars, including our works in this area. 7Thietanosyl Nucleosides

show abstract

“…57-58 "C (0-1 mm), to give 2.40 g (67 %) of trans-l,2cyclobutanedicarbonyl chloride. 12 The dicarbonyl chloride was treated as described above in the case of Feist's perester to give a white, homogeneous solid, m.p. 37-39 "C, after suitable purification via Florisil column chromatography.…”

mentioning

confidence: 99%

The mass spectrometry of some t‐butyl peresters

Krull

Mandelbaum

1976

Org. Mass Spectrom.

View full text Add to dashboard Cite

Mass spectrometry is suggested as a method for the general characterization of mono-and di-f-butyl peresters. In many instances it is possible to measure the molecular ion, especially in the mono-t-butyl peresters. The fragmentation patterns of various t-butyl peresters are presented.ALTHOUGH various methods exist for the characterization of peresters, e.g. infrared spectroscopy, titrimetric analysis and elemental analysis, the use of mass spectrometry for this purpose has been rather 1imited.l One of the problems in measuring the mass spectrum of peresters is the thermal instability of these compounds.ld However, it should be noted that the mass spectra of several other groups of thermally unstable compounds, e.g. peroxides,2-6 hydroperoxides,' ozonidess and azides,$ have been reported.During the course of certain research involving the synthesis of Feist's perester the mass spectrum of this compound was routinely measured. Surprisingly, perester 8 exhibited a distinct molecular ion.l0 This observation prompted us to measure the mass spectra of several other t-butyl peresters and to determine the applicability of mass spectrometry for the characterization of this particular class of organic compounds. We have now measured the mass spectra of seven peresters in the monocarboxylic acid series (1-4) and six in the dicarboxylic acid series (8-13). CO3t-Bu 6 1 C03t-BU Cost-BU 11 aC03t-B~ o C O 3 t -B U C03t-Bu 'CO,t-BU

show abstract

Synthesis of Cyclopropane Derivatives. Precursors for Dimethylenecyclopropane and Trimethylenecyclopropane

Abstract: Moritani for their invaluable sug-gestions in this work, and they are also indebted to the Ministry of Education for the partial financial support of this research.

Cited by 42 publications

References 0 publications

Esters of Feist's Acid: Some Insights into the Electronic Structure and Reactivity of Methylenecyclopropanes Ring‐Substituted with Acceptor Groups

Esters of Feist's Acid: Some Insights into the Electronic Structure and Reactivity of Methylenecyclopropanes Ring‐Substituted with Acceptor Groups

Syntheses of Oxetanocin A and Related Unusual Nucleosides with Bis(hydroxymethyl)-branched Sugars

The mass spectrometry of some t‐butyl peresters

Contact Info

Product

Resources

About