1,1'-Diacetyloctamethylferrocene: An overlooked and overdue synthon leading to the facile synthesis of an octamethylferrocenophane

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Abstract

© 2016 The Royal Society of Chemistry.
This paper describes the facile preparation of 1,1'-diacetyloctamethylferrocene (2) by acylation of octamethylferrocene (1) with acetyl chloride. Chloroformylation with POCl3/DMF of 2 affords a variety of products, including 1,1'-bis-(1-chlorovinyl)octamethylferrocene (3b) in high yield. Compound 3b cyclises in aqueous sodium hydroxide/DMF to an octamethyl[1,4]-ferrocenophane bearing a 1-dimethylaminobuta-1,3-diene-handle (4).
Original languageEnglish
Pages (from-to)18817-18821
Number of pages5
JournalDalton Transactions
Volume45
Issue number47
Early online date17 Oct 2016
DOIs
Publication statusPublished - Dec 2016

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Bearings (structural)
Acylation
Sodium Hydroxide
acetyl chloride

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@article{2b73feca255d43fca7f7b3d9df03a002,
title = "1,1'-Diacetyloctamethylferrocene: An overlooked and overdue synthon leading to the facile synthesis of an octamethylferrocenophane",
abstract = "{\circledC} 2016 The Royal Society of Chemistry.This paper describes the facile preparation of 1,1'-diacetyloctamethylferrocene (2) by acylation of octamethylferrocene (1) with acetyl chloride. Chloroformylation with POCl3/DMF of 2 affords a variety of products, including 1,1'-bis-(1-chlorovinyl)octamethylferrocene (3b) in high yield. Compound 3b cyclises in aqueous sodium hydroxide/DMF to an octamethyl[1,4]-ferrocenophane bearing a 1-dimethylaminobuta-1,3-diene-handle (4).",
author = "Max Roemer and Skelton, {Brian W.} and Piggott, {Matthew J.} and Koutsantonis, {George A.}",
year = "2016",
month = "12",
doi = "10.1039/c6dt03820d",
language = "English",
volume = "45",
pages = "18817--18821",
journal = "Dalton Transactions: the international journal for inorganic, organometallic and bioinorganic chemistry",
issn = "1477-9226",
publisher = "ROYAL SOC CHEMISTRY",
number = "47",

}

TY - JOUR

T1 - 1,1'-Diacetyloctamethylferrocene: An overlooked and overdue synthon leading to the facile synthesis of an octamethylferrocenophane

AU - Roemer, Max

AU - Skelton, Brian W.

AU - Piggott, Matthew J.

AU - Koutsantonis, George A.

PY - 2016/12

Y1 - 2016/12

N2 - © 2016 The Royal Society of Chemistry.This paper describes the facile preparation of 1,1'-diacetyloctamethylferrocene (2) by acylation of octamethylferrocene (1) with acetyl chloride. Chloroformylation with POCl3/DMF of 2 affords a variety of products, including 1,1'-bis-(1-chlorovinyl)octamethylferrocene (3b) in high yield. Compound 3b cyclises in aqueous sodium hydroxide/DMF to an octamethyl[1,4]-ferrocenophane bearing a 1-dimethylaminobuta-1,3-diene-handle (4).

AB - © 2016 The Royal Society of Chemistry.This paper describes the facile preparation of 1,1'-diacetyloctamethylferrocene (2) by acylation of octamethylferrocene (1) with acetyl chloride. Chloroformylation with POCl3/DMF of 2 affords a variety of products, including 1,1'-bis-(1-chlorovinyl)octamethylferrocene (3b) in high yield. Compound 3b cyclises in aqueous sodium hydroxide/DMF to an octamethyl[1,4]-ferrocenophane bearing a 1-dimethylaminobuta-1,3-diene-handle (4).

U2 - 10.1039/c6dt03820d

DO - 10.1039/c6dt03820d

M3 - Article

VL - 45

SP - 18817

EP - 18821

JO - Dalton Transactions: the international journal for inorganic, organometallic and bioinorganic chemistry

JF - Dalton Transactions: the international journal for inorganic, organometallic and bioinorganic chemistry

SN - 1477-9226

IS - 47

ER -