Issue 61, 2021

Synthesis of novel six-, seven- and eight-membered aluminum-containing rings by alumole ring expansion

Abstract

The chemistry of aluminacyclopentadienes, also known as alumoles, has experienced a resurgence in recent years, resulting in the preparation of a number of new entries in this class of compound. In contrast, their reactivity remains relatively unexplored. Thus far, their Lewis acid–base chemistry has been studied, as well as various ring-insertion reactions with unsaturated species such as alkynes and azides. Herein we present a range of new ring expansion reactions of an alumole with heteroatom-containing unsaturated species, providing novel six-, seven- and eight-membered cyclic products with high heteroatom content. Additionally, an unusual reaction was observed when the alumole was treated with morpholine-N-oxide, involving a stepwise insertion of two oxygen atoms, first into the exocyclic Al–C bond and then the endocyclic Al–C bond.

Graphical abstract: Synthesis of novel six-, seven- and eight-membered aluminum-containing rings by alumole ring expansion

Supplementary files

Article information

Article type
Communication
Submitted
07 Eka. 2021
Accepted
29 Eka. 2021
First published
29 Eka. 2021

Chem. Commun., 2021,57, 7505-7508

Synthesis of novel six-, seven- and eight-membered aluminum-containing rings by alumole ring expansion

R. Drescher, B. Ritschel, R. D. Dewhurst, A. Deißenberger, A. Hofmann and H. Braunschweig, Chem. Commun., 2021, 57, 7505 DOI: 10.1039/D1CC02993B

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