Iron and copper catalyzed reaction of benzylamine with carbon tetrachloride

facile formation of 2,4,5- triphenylimidazoline derivatives

Jiro Tsuji, Kiyomi Sakai, Hisao Nemoto, Hideo Nagashima

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Iron and copper salts catalyzed the reaction of benzylamine with CCl4 to give a mixture of 2,4,5-triphenylimidazole (1), 1-benzyl-2,4,5-triphenylimidazole (2), 2,4,5-triphenylimidazoline (3), and 1-benzyl-2,4,5-triphenylimidazoline (4) in high yields. The imidazoline 4 was obtained as the main product. The imidazole and imidazoline derivatives were also formed by the iron-catalyzed reaction of benzylidenebenzylamine (8) or dibenzylamine (5) with CCl4. The imidazoline 4 slowly underwent debenzylation and dehydrogenation with the aid of CCl4 and iron catalyst to give 1 and 2. From these results, a mechanism involving formation of 5 and 8, subsequent oxidative dimerization of 5 and 8 to form 4, and further conversion of 4 to 1, 2, and 3 is proposed.

Original languageEnglish
Pages (from-to)169-176
Number of pages8
JournalJournal of Molecular Catalysis
Volume18
Issue number2
DOIs
Publication statusPublished - Jan 1 1983

Fingerprint

Carbon tetrachloride
Iron
Derivatives
Copper
Dimerization
Dehydrogenation
Salts
Catalysts

All Science Journal Classification (ASJC) codes

  • Engineering(all)

Cite this

Iron and copper catalyzed reaction of benzylamine with carbon tetrachloride : facile formation of 2,4,5- triphenylimidazoline derivatives. / Tsuji, Jiro; Sakai, Kiyomi; Nemoto, Hisao; Nagashima, Hideo.

In: Journal of Molecular Catalysis, Vol. 18, No. 2, 01.01.1983, p. 169-176.

Research output: Contribution to journalArticle

@article{5471c6d679fd4c31991f1b970fbe91c1,
title = "Iron and copper catalyzed reaction of benzylamine with carbon tetrachloride: facile formation of 2,4,5- triphenylimidazoline derivatives",
abstract = "Iron and copper salts catalyzed the reaction of benzylamine with CCl4 to give a mixture of 2,4,5-triphenylimidazole (1), 1-benzyl-2,4,5-triphenylimidazole (2), 2,4,5-triphenylimidazoline (3), and 1-benzyl-2,4,5-triphenylimidazoline (4) in high yields. The imidazoline 4 was obtained as the main product. The imidazole and imidazoline derivatives were also formed by the iron-catalyzed reaction of benzylidenebenzylamine (8) or dibenzylamine (5) with CCl4. The imidazoline 4 slowly underwent debenzylation and dehydrogenation with the aid of CCl4 and iron catalyst to give 1 and 2. From these results, a mechanism involving formation of 5 and 8, subsequent oxidative dimerization of 5 and 8 to form 4, and further conversion of 4 to 1, 2, and 3 is proposed.",
author = "Jiro Tsuji and Kiyomi Sakai and Hisao Nemoto and Hideo Nagashima",
year = "1983",
month = "1",
day = "1",
doi = "10.1016/0304-5102(83)80116-3",
language = "English",
volume = "18",
pages = "169--176",
journal = "Journal of Molecular Catalysis",
issn = "0304-5102",
publisher = "Elsevier BV",
number = "2",

}

TY - JOUR

T1 - Iron and copper catalyzed reaction of benzylamine with carbon tetrachloride

T2 - facile formation of 2,4,5- triphenylimidazoline derivatives

AU - Tsuji, Jiro

AU - Sakai, Kiyomi

AU - Nemoto, Hisao

AU - Nagashima, Hideo

PY - 1983/1/1

Y1 - 1983/1/1

N2 - Iron and copper salts catalyzed the reaction of benzylamine with CCl4 to give a mixture of 2,4,5-triphenylimidazole (1), 1-benzyl-2,4,5-triphenylimidazole (2), 2,4,5-triphenylimidazoline (3), and 1-benzyl-2,4,5-triphenylimidazoline (4) in high yields. The imidazoline 4 was obtained as the main product. The imidazole and imidazoline derivatives were also formed by the iron-catalyzed reaction of benzylidenebenzylamine (8) or dibenzylamine (5) with CCl4. The imidazoline 4 slowly underwent debenzylation and dehydrogenation with the aid of CCl4 and iron catalyst to give 1 and 2. From these results, a mechanism involving formation of 5 and 8, subsequent oxidative dimerization of 5 and 8 to form 4, and further conversion of 4 to 1, 2, and 3 is proposed.

AB - Iron and copper salts catalyzed the reaction of benzylamine with CCl4 to give a mixture of 2,4,5-triphenylimidazole (1), 1-benzyl-2,4,5-triphenylimidazole (2), 2,4,5-triphenylimidazoline (3), and 1-benzyl-2,4,5-triphenylimidazoline (4) in high yields. The imidazoline 4 was obtained as the main product. The imidazole and imidazoline derivatives were also formed by the iron-catalyzed reaction of benzylidenebenzylamine (8) or dibenzylamine (5) with CCl4. The imidazoline 4 slowly underwent debenzylation and dehydrogenation with the aid of CCl4 and iron catalyst to give 1 and 2. From these results, a mechanism involving formation of 5 and 8, subsequent oxidative dimerization of 5 and 8 to form 4, and further conversion of 4 to 1, 2, and 3 is proposed.

UR - http://www.scopus.com/inward/record.url?scp=0347274413&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0347274413&partnerID=8YFLogxK

U2 - 10.1016/0304-5102(83)80116-3

DO - 10.1016/0304-5102(83)80116-3

M3 - Article

VL - 18

SP - 169

EP - 176

JO - Journal of Molecular Catalysis

JF - Journal of Molecular Catalysis

SN - 0304-5102

IS - 2

ER -