Synthesis of 4-(omega-X-alkyl)benzonitriles (X=1,3-dioxan-2-yl, CN, CO2Et) by the reaction of terephthalonitrile dianion with omega-X-alkyl bromides in liquid ammonia

Synthesis of 4-(omega-X-alkyl)benzonitriles (X=1,3-dioxan-2-yl, CN, CO2Et) by the reaction of terephthalonitrile dianion with omega-X-alkyl bromides in liquid ammonia Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2016, Volume: 65, Number: 10, Pages: 2430-2436 Pages count : DOI: 10.1007/s11172-016-1602-x

Tags

terephthalonitrile; benzonitrile; reductive alkylation; alkyl bromides; dianions; radical anions

Authors

Peshkov R. Yu. ^1,2 , Chynyan Wang ^2,3 , Panteleeva E. V. ^1,2,4 , Tretyakov E. V. ^1,2 , Shteingarts V. D. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Prosp Acad Lavrentiev, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 2 Ul Pirogova, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian China Inst Heilongjiang Univ, 74 Xuefu Rd, Harbin 150080, Peoples R China
4	(Данные Web of science) Heilongjiang Univ, Xuefu Rd 74, Harbin 150080, Peoples R China

The main products of the reaction of terephthalonitrile dianion disodium salt with omega-X-alkyl bromides (2-(2-bromoethyl)-1,3-dioxane, 5-bromovaleronitrile, ethyl 6-bromohexanoate) in liquid ammonia are the corresponding 4-(omega-X-alkyl)benzonitriles. Similar reactions of benzonitrile radical anion sodium salt lead to omega-X-alkylbenzenes. In both cases the formation of products is due to selective ipso-alkylation of anionic forms that indicates the nucleophilic activity of terephthalonitrile dianion and benzonitrile radical anion in these reactions and the realization of alkylation via S (N) 2 mechanism.

Peshkov R.Y. , Chynyan W. , Panteleeva E.V. , Tretyakov E.V. , Shteingarts V.D.
Synthesis of 4-(omega-X-alkyl)benzonitriles (X=1,3-dioxan-2-yl, CN, CO2Et) by the reaction of terephthalonitrile dianion with omega-X-alkyl bromides in liquid ammonia
Russian Chemical Bulletin. 2016. V.65. N10. P.2430-2436. DOI: 10.1007/s11172-016-1602-x WOS Scopus РИНЦ

Пешков Р.Ю. , Чуньянь В. , Пантелеева Е.В. , Третьяков Е.В. , Штейнгарц В.Д.
Синтез 4-(ω-x-алкил)бензонитрилов (x - 1,3-диоксан-2-ил, cn, co2et) взаимодействием дианиона терефталонитрила с ω-x-алкилбромидами в жидком аммиаке
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2016. №10. С.2430-2436. РИНЦ

Published print:	Oct 1, 2016
Published online:	May 6, 2017

Web of science	WOS:000400770800019
Scopus	2-s2.0-85018301925
Elibrary	31025631
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