Issue 6, 2015

Sulfur-containing stable five-membered “cycloallene” complexes: 1-thia-2-zircona- and 1-thia-2-titanacyclopenta-3,4-dienes

Abstract

Stable five-membered metallacyclic allenes that contain a sulfur atom were synthesized and structurally characterized. Low-valent zirconocene and titanocene reacted with alkynylthioamides to afford 1-thia-2-metallacyclopenta-3,4-diene compounds in moderate to excellent yields. The molecular structure of the zirconium complexes indicated their cycloallene structure, while an η2-alkyne-coordinated structure might be more responsible for the titanium complexes. Hydrolysis of the compounds gave the corresponding (Z)-alkenylthioamides predominantly. Deuterolysis resulted in >99% D incorporation.

Graphical abstract: Sulfur-containing stable five-membered “cycloallene” complexes: 1-thia-2-zircona- and 1-thia-2-titanacyclopenta-3,4-dienes

Supplementary files

Article information

Article type
Research Article
Submitted
05 Cig 2015
Accepted
08 Agd 2015
First published
13 Agd 2015

Org. Chem. Front., 2015,2, 681-687

Author version available

Sulfur-containing stable five-membered “cycloallene” complexes: 1-thia-2-zircona- and 1-thia-2-titanacyclopenta-3,4-dienes

N. Suzuki, T. Asada, A. Kawamura and Y. Masuyama, Org. Chem. Front., 2015, 2, 681 DOI: 10.1039/C5QO00072F

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