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

4 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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Roemer, M., Skelton, B. W., Piggott, M. J., & Koutsantonis, G. A. (2016). 1,1′-diacetyloctamethylferrocene: an overlooked and overdue synthon leading to the facile synthesis of an octamethylferrocenophane. Dalton Transactions, 45(47), 18817-18821. https://doi.org/10.1039/c6dt03820d

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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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10.1039/c6dt03820d