2-トリメチルシリル-1,3-ジチアン

2-トリメチルシリル-1,3-ジチアン 価格

2-トリメチルシリル-1,3-ジチアン 化学特性,用途語,生産方法

• 外観

  無色～うすい黄色～うすい黄赤色透明液体

• 化学的特性

  CLEAR COLORLESS TO SLIGHTLY YELLOW LIQUID

• 物理的性質

  bp 54–55 °C/0.17 mmHg.

• 使用

  2-Trimethylsilyl-1,3-dithiane is the precursor of dithioketene acetals which are good substrates for both cationic and anionic cyclization processes; the anion reacts with unsaturated ketones and aldehydes to give vinyl dithioketene acetals that can be used as dienes or for the preparation of substituted α,β-unsaturated alkyl ketones; alkylation of the anion provides a general synthesis of acylsilanes. It participates the following reactions: Thioketene Acetals, Cationic and Anionic Cyclizations, Unsaturated Dithioketene Acetals, Acylsilanes, Multicomponent Linchpin Reactions, Formation of Bis(acylsilanes) etc.

• 製造方法

  2-Trimethylsilyl-1,3-dithiane is prepared by alkylation of 2-lithio-1,3- dithiane with chlorotrimethylsilane (eq 1).

• 一般的な説明

  2-(Trimethylsilyl)-1,3-dithiane participates in Lewis base-catalyzed 1,3-dithiane addition to electrophiles such as carbonyl compounds and N-substituted aldimines. It undergoes novel diazo transfer reaction with tosyl azide in hexamethylphosphoramide-THF to yield 2-diazo-1,3-dithiane, which on decomposition yields formal carbene adducts. It is a versatile acyl anion equivalent.

• 純化方法

  Fractionally distil the dithiane through an efficient column and collect the fractions that have the correct NMR and IR spectra. 1H NMR (CCl4) 6.36 (SiMe3), 9.87 (SCHS) and dithiane H at 7 and 8 (ratio 1:9:4:2) from Me4Si; UV 244nm ( 711), sh 227nm ( 800). [Corey et al. J Am Chem Soc 89 max 434 1967.]

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