Α-Thio Carbocations (Thionium Ions) as Intermediates in BrØnsted Acid-Catalyzed Reactions of Enone-Derived 1,3-Dithianes and 1,3-Dithiolanes

Christoph Brenninger; Thorsten Bach

doi:10.1007/s11244-018-0905-6

Α-Thio Carbocations (Thionium Ions) as Intermediates in BrØnsted Acid-Catalyzed Reactions of Enone-Derived 1,3-Dithianes and 1,3-Dithiolanes

Christoph Brenninger
, Thorsten Bach

Chair of Organic Chemistry 1

Technical University of Munich

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Abstract: Evidence was collected for the intermediate formation of thionium ions in Brønsted acid-catalyzed [2 + 2] photocycloaddition and electrophilic addition reactions to enone dithianes and dithiolanes. Low-temperature NMR studies helped to elucidate the structure and configuration of the thionium ions and thus support previous and current results obtained by UV/Vis spectroscopy. Graphical Abstract: [Figure not available: see fulltext.].

Original language	English
Pages (from-to)	623-629
Number of pages	7
Journal	Topics in Catalysis
Volume	61
Issue number	7-8
DOIs	https://doi.org/10.1007/s11244-018-0905-6
State	Published - 1 Jun 2018

Keywords

Acid catalysis
Carbocations
Cyclisation
Dithianes
Photocycloaddition
Sulfonium ions

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10.1007/s11244-018-0905-6

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title = "Α-Thio Carbocations (Thionium Ions) as Intermediates in Br{\O}nsted Acid-Catalyzed Reactions of Enone-Derived 1,3-Dithianes and 1,3-Dithiolanes",

abstract = "Abstract: Evidence was collected for the intermediate formation of thionium ions in Br{\o}nsted acid-catalyzed [2 + 2] photocycloaddition and electrophilic addition reactions to enone dithianes and dithiolanes. Low-temperature NMR studies helped to elucidate the structure and configuration of the thionium ions and thus support previous and current results obtained by UV/Vis spectroscopy. Graphical Abstract: [Figure not available: see fulltext.].",

keywords = "Acid catalysis, Carbocations, Cyclisation, Dithianes, Photocycloaddition, Sulfonium ions",

author = "Christoph Brenninger and Thorsten Bach",

note = "Publisher Copyright: {\textcopyright} 2018, The Author(s).",

year = "2018",

month = jun,

day = "1",

doi = "10.1007/s11244-018-0905-6",

language = "English",

volume = "61",

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TY - JOUR

T1 - Α-Thio Carbocations (Thionium Ions) as Intermediates in BrØnsted Acid-Catalyzed Reactions of Enone-Derived 1,3-Dithianes and 1,3-Dithiolanes

AU - Brenninger, Christoph

AU - Bach, Thorsten

PY - 2018/6/1

Y1 - 2018/6/1

N2 - Abstract: Evidence was collected for the intermediate formation of thionium ions in Brønsted acid-catalyzed [2 + 2] photocycloaddition and electrophilic addition reactions to enone dithianes and dithiolanes. Low-temperature NMR studies helped to elucidate the structure and configuration of the thionium ions and thus support previous and current results obtained by UV/Vis spectroscopy. Graphical Abstract: [Figure not available: see fulltext.].

AB - Abstract: Evidence was collected for the intermediate formation of thionium ions in Brønsted acid-catalyzed [2 + 2] photocycloaddition and electrophilic addition reactions to enone dithianes and dithiolanes. Low-temperature NMR studies helped to elucidate the structure and configuration of the thionium ions and thus support previous and current results obtained by UV/Vis spectroscopy. Graphical Abstract: [Figure not available: see fulltext.].

KW - Acid catalysis

KW - Carbocations

KW - Cyclisation

KW - Dithianes

KW - Photocycloaddition

KW - Sulfonium ions

UR - https://www.scopus.com/pages/publications/85048334026

U2 - 10.1007/s11244-018-0905-6

DO - 10.1007/s11244-018-0905-6

M3 - Article

AN - SCOPUS:85048334026

SN - 1022-5528

VL - 61

SP - 623

EP - 629

JO - Topics in Catalysis

JF - Topics in Catalysis

IS - 7-8

ER -

Α-Thio Carbocations (Thionium Ions) as Intermediates in BrØnsted Acid-Catalyzed Reactions of Enone-Derived 1,3-Dithianes and 1,3-Dithiolanes

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