Abstract
Thianthrene cation radical perchlorate () reacted readily with two isomeric thiols, benzylthiol (1) and 4-methylbenzenethiol (7) in an acetonitrile solution at room temperature. From the reaction of 1, the major products, N-benzylacetamide (4) and benzyl sulfide (5), are characteristic of benzyl carbocations while the minor one, benzyl disulfide (6) implies free radical component of the reaction. It is unprecedented that the formation of a benzyl carbocation was caused by the extrusion of sulfur atoms from benzyl sulfur cations (3). In contrast, from the reaction of 7, only p-tolyl disulfide (10) was obtained from both sulfur radicals and cations. In the reaction of 7 the thio-extrusion was not observed from the p-tolyl sulfur cation (9). A thianthrene cation radical () was reduced quantitatively to thianthrene (Th) in both reactions.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
