Reactions of Allenyltri-n-butylstannane with Halides of Phosphorus, Arsenic, Antimony, Germanium, Tin, and Boron. Preparation of Propargylic and/or Allenic Derivatives

doi:10.1021/OM990543L

Paper

Reactions of Allenyltri-n-butylstannane with Halides of Phosphorus, Arsenic, Antimony, Germanium, Tin, and Boron. Preparation of Propargylic and/or Allenic Derivatives

Published Nov 10, 1999 · J. Guillemin, Karine Malagu

Organometallics

Q1 SJR score

24

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0

Influential Citations

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Abstract

The reaction of allenyltri-n-butylstannane with a phosphorus or arsenic trihalide and with germanium tetrachloride gave the corresponding propargylic halophosphine, arsine, or germane. When they were heated, the propargylic products partially (P, Ge) or completely (As) rearranged into the corresponding allenyl derivatives, the thermodynamic products. The allenic or propargylic stannane reacted with stronger Lewis acidic halides such as a boron halide, antimony trichloride, or tin tetrachloride to give only the allenic product, even when the reaction was performed and analyzed at low temperature (−80 °C). The propargylic intermediate was observed with the antimony and tin compounds when a substituted derivative (e. g. Vi2SbCl, ViSnCl3) was used. The reduction of the propargylic halide products prior to their isomerization gave the corresponding primary propargylic phosphine, arsine, germane, and stannane.

Study Snapshot

Allenyltri-n-butylstannane reacts with phosphorus, arsenic, and germanium halides to produce propargylic and allenic derivatives, with stronger Lewis acidic halides yielding only allenic products.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Reactions of Allenyltri-n-butylstannane with Halides of Phosphorus, Arsenic, Antimony, Germanium, Tin, and Boron. Preparation of Propargylic and/or Allenic Derivatives

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References

Citations

Primary α-Phosphino- and α-Arseno-Nitriles, Analogues of α-Aminonitriles.

-phosphinonitriles and -arsenonitriles have been prepared and characterized, offering new insights into the chemistry of these compounds.

The metal tin promoted cascade reaction of ketones in aqueous media for the construction of 2-bromo-4-aryl-1,3-pentadiene.

Tin promotes a novel cascade reaction in aqueous media, leading to the construction of new, highly functionalized 2-bromo-4-aryl-1,3-pentadienes with good yields and easy operation.

Tributyl‐1,2‐propadien‐1‐yl‐stannane

Tributyl-1,2-propadien-1-yl-stannane is a very toxic compound that should be handled in well-ventilated fume hoods wearing gloves and protective clothing.

Five-membered metallacycloalkynes formed from group 4 metals and [n]cumulene (n = 3,5) ligands

Group 4 metallocene complexes with [3]- and [5]cumulene ligands form 5-membered metallacycles with a "triple bond" and can form bimetallic complexes with transition metals.

Further Advances in Germanium, Tin and Lead NMR

This paper presents further advances in Germanium, Tin, and Lead NMR, focusing on chemical shifts and measurements for various compounds.