A New Route to Silaheterocycles: Nucleophilic Aminomethylation

Hans H. Karsch; Kai A. Schreiber

doi:10.1002/9783527619900.ch36

A New Route to Silaheterocycles: Nucleophilic Aminomethylation

Hans H. 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)CH₂Li, were obtained and isolated. The reaction of both compounds with difunctional chlorosilanes yield six-membered heterocycles including [inlinemath presented] 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 SiCl₄. The compounds have been characterized by mass,¹H,¹³C, and²⁹Si NMR spectroscopy and elemental analysis.

Original language	English
Title of host publication	Organosilicon Chemistry III
Subtitle of host publication	From Molecules to Materials
Publisher	wiley
Pages	237-240
Number of pages	4
ISBN (Electronic)	9783527619900
ISBN (Print)	9783527620746
DOIs	https://doi.org/10.1002/9783527619900.ch36
State	Published - 1 Jan 2008

Keywords

Aminomethylation
Diazasilaheterocycles
Lithium methylamines

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10.1002/9783527619900.ch36

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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)CH2Li, were obtained and isolated. The reaction of both compounds with difunctional chlorosilanes yield six-membered heterocycles including [inlinemath presented] 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 SiCl4. The compounds have been characterized by mass,1H,13C, and29Si NMR spectroscopy and elemental analysis.",

keywords = "Aminomethylation, Diazasilaheterocycles, Lithium methylamines",

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

note = "Publisher Copyright: {\textcopyright} WILEY-VCH Verlag GmbH, D-69469 Weinheim (Federal Republic of Germany), 1998.",

year = "2008",

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doi = "10.1002/9783527619900.ch36",

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TY - CHAP

T1 - A New Route to Silaheterocycles

T2 - Nucleophilic Aminomethylation

AU - Karsch, Hans H.

AU - Schreiber, Kai A.

N1 - Publisher Copyright: © WILEY-VCH Verlag GmbH, D-69469 Weinheim (Federal Republic of Germany), 1998.

PY - 2008/1/1

Y1 - 2008/1/1

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)CH2Li, were obtained and isolated. The reaction of both compounds with difunctional chlorosilanes yield six-membered heterocycles including [inlinemath presented] 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 SiCl4. The compounds have been characterized by mass,1H,13C, and29Si 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)CH2Li, were obtained and isolated. The reaction of both compounds with difunctional chlorosilanes yield six-membered heterocycles including [inlinemath presented] 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 SiCl4. The compounds have been characterized by mass,1H,13C, and29Si NMR spectroscopy and elemental analysis.

KW - Aminomethylation

KW - Diazasilaheterocycles

KW - Lithium methylamines

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U2 - 10.1002/9783527619900.ch36

DO - 10.1002/9783527619900.ch36

M3 - Chapter

AN - SCOPUS:85214760416

SN - 9783527620746

SP - 237

EP - 240

BT - Organosilicon Chemistry III

PB - wiley

ER -

A New Route to Silaheterocycles: Nucleophilic Aminomethylation

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