Reactions of α,β-Unsaturated Ketone Acetals with Trimethylsilyl Cyanide and Trimethylsilyl Sulfides

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On the Reactions of CF3SF4C1, (CF3)2SF2, SF4, and 0SC12 with Trimethylsilyl Cyanide

A moderately stable hexacoordinated sulfur(VI) compound with four different kinds of ligands, CF3SF2(CN)2C1, results when CF3SF4CI is reacted with (CH3)3SiCN. The latter compound also gives F2S(CN)2 and (CF3)2S(CN)2 with SF4 and (CF3)2SF2, respectively. These tetracoordinated suifur(IV) compounds decompose rapidly at 25 °C but are stable at lower temperatures. With OSCl2 and SC12, the white sol...

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Difluorocarbene, generated from trimethylsilyl fluorosulfonyldifluoroacetate (TFDA), reacts with the uridine and adenosine substrates preferentially at the enolizable amide moiety of the uracil ring and the 6-amino group of the purine ring. 2',3'-Di-O-acetyl-3'-deoxy-3'-methyleneuridine reacts with TFDA to produce 4-O-difluoromethyl product derived from an insertion of difluorocarbene into the ...

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Reactions of 9H-Fluorene-9-thione with (Trimethylsilyl)- diazomethane*

The [3+2]-cycloaddition of (trimethylsilyl)diazomethane (7) with 9H-fluorene-9-thione (1) at –60°C yields the spirocyclic 2,5-dihydro-5-trimethylsilyl-1,3,4-thiadiazole 10, which eliminates nitrogen at room temperature to give the 1,4-dithiane derivative 13 by dimerization of the intermediate fluorenethione (trimethylsilyl)methanide (11). This thiocarbonyl ylide can be trapped by 1 to give the ...

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Mild deprotection of methylene acetals in combination with trimethylsilyl triflate-2,2'-bipyridyl.

The facile deprotection of methylene acetal protection of diols under mild conditions is established. The combination of trimethylsilyl triflate (TMSOTf) and 2,2'-bipyridyl followed by a weakly acidic hydrolysis was effective and the substrates having acid sensitive functional groups can be tolerated under the stated conditions. The selective deprotection between methylene acetal and benzopheno...

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Phosphotungstic Acidcatalyzed Strecker Three-Component Reaction of Amino Acids, Aldehydes, and Trimethylsilyl Cyanide

A simple and efficient one-pot, three-component Strecker reaction of protected amino acids, aromatic aldehydes, and trimethylsilyl cyanide has been developed for the synthesis of chiral α-amino nitriles. The reaction was carried out in the presence of catalytic amount of phosphotungstic acid (H3[P(W3O10)4]) as an environmentally friendly cata...

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ژورنال

عنوان ژورنال: Bulletin of the Chemical Society of Japan

سال: 1991

ISSN: 0009-2673,1348-0634

DOI: 10.1246/bcsj.64.1108