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

Dalton Trans. 2016 Dec 21;45(47):18817-18821. doi: 10.1039/c6dt03820d. Epub 2016 Oct 24.

Authors

Max Roemer¹, Brian W Skelton, Matthew J Piggott, George A Koutsantonis

Affiliation

¹ Chemistry, M310, School of Chemistry and Biochemistry, The University of Western Australia, 35 Stirling Hwy, Crawley, WA 6009, Australia. max.roemer@uwa.edu.au george.koutsantonis@uwa.edu.au.

PMID: 27774559
DOI: 10.1039/c6dt03820d

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).