The Synthesis of Cyclic Alcohols and Olefins by the Interaction of Dimagnesium Halides and Esters

Nenitzescu, Costin D.; Necsoiu, I.

doi:10.1021/ja01164a046

Cited by 23 publications

(3 citation statements)

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“…This diol (prisms, mp 134 "C) was made by known procedures (5,6). An intermediate in the hydrogenation of 1,l'-ethynylenedicyclopentanol was identified as the cis isomer (cf.…”

Section: L'-eil~~le~~edic~clope~zranol (I)mentioning

confidence: 99%

Dehydration of 1,1′-ethylenedicyclopentanol

Diaper¹

1976

Can. J. Chem.

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“…This diol (prisms, mp 134 "C) was made by known procedures (5,6). An intermediate in the hydrogenation of 1,l'-ethynylenedicyclopentanol was identified as the cis isomer (cf.…”

Section: L'-eil~~le~~edic~clope~zranol (I)mentioning

confidence: 99%

Dehydration of 1,1′-ethylenedicyclopentanol

Diaper¹

1976

Can. J. Chem.

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“…Normal-chain alkyldimagnesium halides have been shown to give good yields of dicarboxylic acids on reaction with carbon dioxide. Complications, however, may arise, and instead of the corresponding dicarboxylic acid, coupling and/or cyclization products may be formed (507). Thus, trimethylene dibromide has given suberic acid (755), while sebacic acid and an acid with fourteen carbon atoms were obtained from 1,4-dibromobutane in a similar manner (109), the principal product being the cycloalkanone.…”

Section: T H I S C O N T E N T Imentioning

confidence: 99%

Syntheses Of Alkylated Alkanedioic Acids

Diaper¹,

KUKSIS²

1959

Chem. Rev.

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example of such a synthesis is the conversion of 2-pentenal, through a Reformatsky condensation with ethyl -bromopropionate and oxalation of the unsaturated product, eventually to 2,6-dimethylsuberic acid (401).It has been shown that formates and oxalates may function as carbonyl components in a Reformatsky synthesis. Ethyl -bromoisobutyrate reacts with ethyl oxalate (569) and with ethyl formate (82), giving hydroxy esters which could be converted to 2,2-dimethylsuccinic and 2,2,4,4-tetramethyIglutaric acids, respectively.The application of the Reformatsky reaction to nitriles (154) leads to the formation of ketones in a manner comparable with the Grignard reaction and is a convenient method for the synthesis of /3-keto esters.By varying the nature of the carbonyl compounds and the halo esters employed, many alkylated dicarboxylic acids have been prepared with the help of this reaction, yet the possible products may be of only a few types. Branching is confined to the a-and ß-positions at one or both ends of the chain, and while the -position may bear one, two, or no alkyl groups, the /3-position cannot bear more than one side chain.Theoretically, in all of the above cases the ester groups of the final products may be converted into aldehyde or keto groups through the acyl chlorides and dialkyl metals (142).A repetition of the Reformatsky process would lengthen the chain with or without further branching at the new points of junction of carbon chains (629).

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“…Received January 2,1957 In the course of a synthetic study relatively large quantities of tetramethylene dibromide and chlorobromide were required, and an attempt was made to develop inexpensive methods for the preparation of these substances.…”

Section: Preparation Of Tetramethylene Dibromide and Chlorobromidementioning

confidence: 99%

Notes - Preparation of Tetramethylene Dibromide and Chlorobromide

Kaluszyner¹

1957

J. Org. Chem.

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The Synthesis of Cyclic Alcohols and Olefins by the Interaction of Dimagnesium Halides and Esters

Cited by 23 publications

References 0 publications

Dehydration of 1,1′-ethylenedicyclopentanol

Dehydration of 1,1′-ethylenedicyclopentanol

Syntheses Of Alkylated Alkanedioic Acids

Notes - Preparation of Tetramethylene Dibromide and Chlorobromide

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