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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

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
DOIs	https://doi.org/10.1039/c6dt03820d
Publication status	Published - 21 Dec 2016
Externally published	Yes

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title = "1,1′-diacetyloctamethylferrocene: an overlooked and overdue synthon leading to the facile synthesis of an octamethylferrocenophane",

abstract = "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).",

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AU - Roemer, Max

AU - Skelton, Brian W.

AU - Piggott, Matthew J.

AU - Koutsantonis, George A.

PY - 2016/12/21

Y1 - 2016/12/21

N2 - 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 - 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).

UR - https://www.scopus.com/pages/publications/85000711474

UR - http://purl.org/au-research/grants/arc/DP150104117

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SN - 1477-9226

VL - 45

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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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