Preparation of Novel Photosensitive Polyimide Systems via Long-Lived Active Intermediates

Yamashita, Takahi; Horie, Kazuyuki

doi:10.1021/bk-1994-0537.ch030

ACS Symposium Series

1993

DOI: 10.1021/bk-1994-0537.ch030

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Preparation of Novel Photosensitive Polyimide Systems via Long-Lived Active Intermediates

Takahi Yamashita

Kazuyuki Horie

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2002

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“…10 Compounds 4 were prepared by silylation of the corresponding dithiane followed by hydrolysis. 11 Most of these silicon derivatives were described as labile compounds, except for 2 and 3 where the silicon is substituted by trimethylsilyl groups, limiting the preparative interest of this chemistry.…”

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confidence: 99%

Synthesis of a New Type of Bis(acylsilanes) Starting from 2-Alkyl- or 2-Phenyl-1,3-dithiane and Bis(chlorinated) Disilane or Disiloxane

Bouillon¹,

Huguenot²,

Portella³

2002

Synthesis

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New bis(acylsilanes) 17-19 bearing silicon atoms in an internal position were synthesized via silylation of 2-lithio-2-substituted-1,3-dithianes with bis(chlorinated) disilane 10 or siloxanes 11, 12. The dethioketalization of bis(dithianes) intermediates was performed using iodine and calcium carbonate. The method was efficient and general for linear and substituted alkyl chain derivatives but gave low yields for the aromatic compound 18d.Bis(acylsilanes) [bis(Ac)] are versatile building blocks in organic synthesis because they combine the usual properties of dicarbonyl compounds and the specific properties of acylsilanes 1 [oxygenophilicity (Brook rearrangement) 2 and fluorophilicity 3 of silicon]. There are two types of bis(acylsilanes): the 1,n-bis(silylated) 1,n-alcanediones 1 and the bis(acylsilanes) such as 2 and 3 with the silicon in an internal position (Figure 1). The first class of bis(Ac) 1 is well documented. They are generally prepared using nucleophilic silylation, 4 electrophilic silylation 5 or palladium catalyzed coupling methods. 6 The second series has been less investigated. The monosilylated compounds 2 were synthesized by a two step sequence (bromination followed by hydrolysis) from dibenzylsilanes 7 or by reaction of lithium tris(trimethylsilyl)silenolate with acyl halides. 8 The bis(silylated) derivatives 3 were obtained by oxidative coupling of lithium silenolate (R 2 = TMS) 9 or by the Corey-Brook method (R 2 = Me). 10 Compounds 4 were prepared by silylation of the corresponding dithiane followed by hydrolysis. 11 Most of these silicon derivatives were described as labile compounds, except for 2 and 3 where the silicon is substituted by trimethylsilyl groups, limiting the preparative interest of this chemistry.In this paper we describe an efficient synthesis of new bis(acylsilanes) 4 [X = (CH 2 ) 2 , O, OSiMe 2 O] using a Corey-Brook type methodology. 12 As we have previously reported, 5c the nucleophilic displacement of chlorides from disilane 10 and siloxanes 11, 12 (Figure 2) was performed using lithium derivatives of 2-alkyl-or 2-phenyl-1,3-dithianes 5-9 as carbonyl anion equivalents (Scheme 1, Table 1). Figure 2 Structures of reagents for the Corey-Brook reaction.Scheme 1 Reaction of the lithium derivatives of 2-alkyl-or 2-phenyl-1,3-dithianes 5-9 with disilane 10 and siloxanes 11, 12.

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confidence: 99%

Synthesis of a New Type of Bis(acylsilanes) Starting from 2-Alkyl- or 2-Phenyl-1,3-dithiane and Bis(chlorinated) Disilane or Disiloxane

Bouillon¹,

Huguenot²,

Portella³

2002

Synthesis

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Preparation of Novel Photosensitive Polyimide Systems via Long-Lived Active Intermediates

Cited by 1 publication

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Synthesis of a New Type of Bis(acylsilanes) Starting from 2-Alkyl- or 2-Phenyl-1,3-dithiane and Bis(chlorinated) Disilane or Disiloxane

Synthesis of a New Type of Bis(acylsilanes) Starting from 2-Alkyl- or 2-Phenyl-1,3-dithiane and Bis(chlorinated) Disilane or Disiloxane

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