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

Max Roemer; Brian W. Skelton; Matthew J. Piggott; George A. Koutsantonis

doi:10.1039/c6dt03820d

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

Max Roemer, Brian W. Skelton, Matthew J. Piggott, George A. Koutsantonis

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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 language	English
Pages (from-to)	18817-18821
Number of pages	5
Journal	Dalton Transactions
Volume	45
Issue number	47
Early online date	17 Oct 2016
DOIs	https://doi.org/10.1039/c6dt03820d
Publication status	Published - Dec 2016

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10.1039/c6dt03820d

Roemer_et_al 2016 1,1 '-Diacetyloctamethylferrocene Accepted author manuscript, 376 KBLicence: Unspecified

Molecular Switching and Moore
Koutsantonis, G. (Investigator 01), Nichols, R. (Investigator 02) & Kaupp, M. (Investigator 03)
ARC Australian Research Council
1/01/15 → 9/09/18
Project: Research

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

abstract = "{\textcopyright} 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",

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doi = "10.1039/c6dt03820d",

language = "English",

volume = "45",

pages = "18817--18821",

journal = "Dalton Transactions",

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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

C2 - 27774559

SN - 1477-9226

VL - 45

SP - 18817

EP - 18821

JO - Dalton Transactions

JF - Dalton Transactions

IS - 47

ER -

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

Abstract

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