Abstract:
A dramatical difference in the stereoselectivity of 1,1-dimethylallene allylboration with allyl(chloro)- and triallylboranes has been revealed and applied to the synthesis of isomeric 7-methylene-6,6-dimethyl- and 6-(1-methylethylidene)-3-borabicyclo[3.3.1]-nonanes.
Document Type:
Article
Language: English
Citation:
S. Yu. Erdyakov, M. E. Gurskii, A. V. Ignatenko, Yu. N. Bubnov, “Regioselectivity of 1,1-dimethylallene allylboration: synthesis of isomeric 6- and 7-methylene-3-borabicyclo[3.3.1]nonanes”, Mendeleev Commun., 14:6 (2004), 242–244
Linking options:
https://www.mathnet.ru/eng/mendc3895
https://www.mathnet.ru/eng/mendc/v14/i6/p242
This publication is cited in the following 10 articles:
Xin Tao, Karel Škoch, Constantin G. Daniliuc, Gerald Kehr, Gerhard Erker, “Borane-induced ring closure reaction of oligomethylene-linked bis-allenes”, Chem. Sci., 11:6 (2020), 1542
Xin Tao, Constantin G. Daniliuc, Dustin Dittrich, Gerald Kehr, Gerhard Erker, “Borane‐Induced Dimerization of Arylallenes”, Angew Chem Int Ed, 57:42 (2018), 13922
Xin Tao, Constantin G. Daniliuc, Dustin Dittrich, Gerald Kehr, Gerhard Erker, “Borane‐Induced Dimerization of Arylallenes”, Angewandte Chemie, 130:42 (2018), 14118
Xin Tao, Gerald Kehr, Constantin G. Daniliuc, Gerhard Erker, “Selective Metal‐free HB(C6F5)2 Catalyzed Allene Cyclotrimerization: Formation of 1,3,5‐Trimethylenecyclohexane and Its Tris‐hydroboration Product”, Angewandte Chemie, 129:5 (2017), 1396
Xin Tao, Gerald Kehr, Constantin G. Daniliuc, Gerhard Erker, “Selective Metal‐free HB(C6F5)2 Catalyzed Allene Cyclotrimerization: Formation of 1,3,5‐Trimethylenecyclohexane and Its Tris‐hydroboration Product”, Angew Chem Int Ed, 56:5 (2017), 1376
Sergey Yu. Erdyakov, Anatolii V. Ignatenko, Tamara V. Potapova, Konstantin A. Lyssenko, Mikhail E. Gurskii, Yuri N. Bubnov, “Design of Bicyclic and Cage Boron Compounds Based on Allylboration of Acetylenes with Allyldichloroboranes”, Org. Lett., 11:13 (2009), 2872
S. Yu. Erdyakov, A. V. Ignatenko, M. E. Gurskii, Yu. N. Bubnov, “Reactions of boron trifluoride with allylic boranes and 1-boraadamantane”, Mendeleev Commun., 17:5 (2007), 271–273
S. Yu. Erdyakov, S. V. Stefanyuk, A. V. Ignatenko, M. E. Gurskii, Yu. N. Bubnov, “Stereoselectivity of allylboron–acetylene condensation with crotylic boranes: synthesis of 4-methyl-1-boraadamantane derivatives”, Mendeleev Commun., 17:3 (2007), 139–141
Sergey Yu. Erdyakov, Mikhail E. Gurskii, Anatolii V. Ignatenko, Yurii N. Bubnov, “Regioselectivity of 1,1‐Dimethylallene Allylboration: Synthesis of Isomeric 6‐ and 7‐Methylene‐3‐borabicyclo[3.3.1]nonanes.”, ChemInform, 36:22 (2005)
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