Observation of a Thermally Induced Bora-Nazarov Cyclization at a Phosphole Framework†
Dr. Juri Möbus
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Present address: Department of Chemistry, University of Toronto, 80 St. George Street, M5S 3H6, Toronto, Ontario (Canada)
Search for more papers by this authorDr. Gerald Kehr
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Search for more papers by this authorDr. Constantin G. Daniliuc
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Search for more papers by this authorDr. Christian Mück-Lichtenfeld
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Gerhard Erker
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)Search for more papers by this authorDr. Juri Möbus
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Present address: Department of Chemistry, University of Toronto, 80 St. George Street, M5S 3H6, Toronto, Ontario (Canada)
Search for more papers by this authorDr. Gerald Kehr
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Search for more papers by this authorDr. Constantin G. Daniliuc
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Search for more papers by this authorDr. Christian Mück-Lichtenfeld
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Gerhard Erker
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)Search for more papers by this authorFinancial support from the Deutsche Forschungsgemeinschaft is gratefully acknowledged.
Abstract
The reaction of the bis(enynyl)phosphanes 6 a,b with the electrophilic borane reagents RB(C6F5)2 (R=C6F5, CH2CH2Ph, CH3) gave phospholes cleanly in a 1,1-carboboration reaction sequence. Depending on the steric bulk, the resulting 2,5-alkenylphospholes underwent a thermally induced bora-Nazarov type cyclization. The equilibrium situation of these examples of a bora-Nazarov type cyclization was investigated in detail by NMR spectroscopy, X-ray crystal structure analysis, and DFT calculations.
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