Unexpected course of the attempted conversions of ferrocenyl(hetaryl)methanols into thiols using Lawesson's reagent

GRAPHICAL ABSTRACT

ABSTRACT

A series of secondary methanols bearing ferrocenyl and a hetaryl substituent was tested in reactions with Lawesson's reagent (LR) aimed at the preparation of respective methanethiols. The study showed that in boiling toluene after only few minutes the starting alcohols were consumed and unexpectedly, depending on the type of hetaryl substituent, tetra-substituted ethane or disubstituted methane derivatives were obtained in good to excellent yields. The presence of the ferrocene moiety is crucial for the observed reaction courses.

KEYWORDS:

• Lawesson's reagent
• secondary alcohols
• thiols
• ferrocene derivatives
• thiophene derivatives
• selenophene derivatives

Acknowledgments

We thank PD Dr. L. Bigler, University of Zurich, for the registration of HR-ESI-MS spectra. Skilful help by Ms. H. Jatczak and A. Cieślińska (University of Łódź) in performance of elemental analysis of all reported compounds is gratefully acknowledged.

Funding

The authors acknowledge financial support by the National Science Center (Cracow, Poland) within the Maestro Grant (project number 2012/06A/ST5/00219).