A New Route to Silaheterocycles: Nucleophilic Aminomethylation

Hans Heinz Karsch; Kai A. Schreiber

doi:10.1002/9783527620777.ch36b

A New Route to Silaheterocycles: Nucleophilic Aminomethylation

Hans Heinz Karsch, Kai A. Schreiber

Natural Sciences

Technical University of Munich

Research output: Chapter in Book/Report/Conference proceeding › Chapter › peer-review

Abstract

By metalation of the respective aminals with t-BuLi, two different double lithiated methylmethylenediamines, namely LiCH2N(CH3)CH2N(CH3)CH2Li and LiCH₂N(C₆H₁₁ )CH₂N(C₆H₁₁)CH₂ Li, were obtained and isolated. The reaction of both compounds with difunctional chlorosilanes yield six-membered heterocycles including (CH₃)₂SiCH₂N(CH₃)CH₂N(CH₃)CH₂ by nucleophilic amino methylation. A spiro heterocycle Si[CH₂N(CH₃)CH₂N(CH₃)CH₂]₂ can be synthesized in the same way by using two equivalents of lithiated tetramethylmethylenediamine and SiCI4. The compounds have been characterized by mass, ¹H, ¹³C, and ²⁹Si NMR spectroscopy and elemental analysis.

Original language	English
Title of host publication	Organosilicon Chemistry Set
Subtitle of host publication	From Molecules to Materials
Publisher	wiley
Pages	237-240
Number of pages	4
ISBN (Electronic)	9783527620777
ISBN (Print)	9783527323470
DOIs	https://doi.org/10.1002/9783527620777.ch36b
State	Published - 10 Jun 2008

Keywords

Aminomethylation
Diazasilaheterocycles
Lithium methylamines

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10.1002/9783527620777.ch36b

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title = "A New Route to Silaheterocycles: Nucleophilic Aminomethylation",

abstract = "By metalation of the respective aminals with t-BuLi, two different double lithiated methylmethylenediamines, namely LiCH2N(CH3)CH2N(CH3)CH2Li and LiCH2N(C6H11 )CH2N(C6H11)CH2 Li, were obtained and isolated. The reaction of both compounds with difunctional chlorosilanes yield six-membered heterocycles including (CH3)2SiCH2N(CH3)CH2N(CH3)CH2 by nucleophilic amino methylation. A spiro heterocycle Si[CH2N(CH3)CH2N(CH3)CH2]2 can be synthesized in the same way by using two equivalents of lithiated tetramethylmethylenediamine and SiCI4. The compounds have been characterized by mass, 1H, 13C, and 29Si NMR spectroscopy and elemental analysis.",

keywords = "Aminomethylation, Diazasilaheterocycles, Lithium methylamines",

author = "Karsch, {Hans Heinz} and Schreiber, {Kai A.}",

year = "2008",

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doi = "10.1002/9783527620777.ch36b",

language = "English",

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booktitle = "Organosilicon Chemistry Set",

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TY - CHAP

T1 - A New Route to Silaheterocycles

T2 - Nucleophilic Aminomethylation

AU - Karsch, Hans Heinz

AU - Schreiber, Kai A.

PY - 2008/6/10

Y1 - 2008/6/10

N2 - By metalation of the respective aminals with t-BuLi, two different double lithiated methylmethylenediamines, namely LiCH2N(CH3)CH2N(CH3)CH2Li and LiCH2N(C6H11 )CH2N(C6H11)CH2 Li, were obtained and isolated. The reaction of both compounds with difunctional chlorosilanes yield six-membered heterocycles including (CH3)2SiCH2N(CH3)CH2N(CH3)CH2 by nucleophilic amino methylation. A spiro heterocycle Si[CH2N(CH3)CH2N(CH3)CH2]2 can be synthesized in the same way by using two equivalents of lithiated tetramethylmethylenediamine and SiCI4. The compounds have been characterized by mass, 1H, 13C, and 29Si NMR spectroscopy and elemental analysis.

AB - By metalation of the respective aminals with t-BuLi, two different double lithiated methylmethylenediamines, namely LiCH2N(CH3)CH2N(CH3)CH2Li and LiCH2N(C6H11 )CH2N(C6H11)CH2 Li, were obtained and isolated. The reaction of both compounds with difunctional chlorosilanes yield six-membered heterocycles including (CH3)2SiCH2N(CH3)CH2N(CH3)CH2 by nucleophilic amino methylation. A spiro heterocycle Si[CH2N(CH3)CH2N(CH3)CH2]2 can be synthesized in the same way by using two equivalents of lithiated tetramethylmethylenediamine and SiCI4. The compounds have been characterized by mass, 1H, 13C, and 29Si NMR spectroscopy and elemental analysis.

KW - Aminomethylation

KW - Diazasilaheterocycles

KW - Lithium methylamines

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U2 - 10.1002/9783527620777.ch36b

DO - 10.1002/9783527620777.ch36b

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SN - 9783527323470

SP - 237

EP - 240

BT - Organosilicon Chemistry Set

PB - wiley

ER -

A New Route to Silaheterocycles: Nucleophilic Aminomethylation

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Keywords

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