71338-99-3Relevant academic research and scientific papers
Norbornanes. Part 10. Solvolysis of the Stereoisomeric 6-cyano-2-norbornyl p-Toluenesulfonates. A Correction
Grob, Cyril A.,Herzfeld, Danielle
, p. 2443 - 2447 (1982)
The solvolysis products of the stereoisomeric 6-cyano-2-norbornyl p-toluenesulfonates 1-4 (R = CN) in dioxane/water 7 : 3 have been determined.In contrast to an earlier report the 6exo-cyano-2exo-norbornyl p-toluenesulfonate (1; R = CN) yields 30percent of the 2endo-alcohol 9 (R = CN) beside the 2exo-alcohol 10 and the norbornenes 12 and 13.The results confirm that -I substituents at C(6) reduce 1,3-bridging in the intermediate norbornyl cation and hence its rate of rearrangement.The relatively high rate constants for some 6-fluoro- and 6-cyano-2exo-norbornyl p-toluenesulfonates are ascribed to C,C-hyperconjugation assisted by the conjugative effects of the 6-fluoro and cyano substituents.
Rearrangements of 5- and 6-Cyano-2-norbornyl Cations
Fermann, Michael,Herpers, Ekkehard,Kirmse, Wolfgang,Neubauer, Regina,Renneke, Franz-Josef,et al.
, p. 975 - 984 (2007/10/02)
Hydroboration of the 5-norbornene-2-carbonitriles 11 afforded 5- and 6-hydroxynorbornane-2-carbonitriles (9a, 10a) along with the analogous ketones 12, 13. 5- and 6-aminonorbornane-2-carbonitriles (17a, 18a) were obtained either from the endo-brosylates 1
Synthese und Hydrolyse von 6endo-substituierten p-Toluolsulfonsaeure-estern.
Grob, Cyril A.,Guenther, Bettina,Hanreich, Reinhard
, p. 2288 - 2298 (2007/10/02)
The Synthesis and Hydrolysis of 6endo-Substituted 2endo-Norbornyl p-Toluenesulfonates; The hydrolysis products of the p-toluenesulfonates of several hitherto unknown 6endo-substituted 2endo-norbornanols have been determined.
The Synthesis of 6-substituted 2-Norbornanols
Grob, Cyril A.,Guenther, Bettina,Waldner, Adrian
, p. 2709 - 2720 (2007/10/02)
The preparation of several 6-exo- and 6-endo-substituted 2-exo- and 2-endo-norbornanols and their p-toluenesulfonates is described.
Die Synthese von 6exo-substituierten p-Toluolsulfonsaeure-estern
Fischer, Walter von,Grob, Cyril A.,Sprecher, Georg von
, p. 806 - 815 (2007/10/02)
A number of hitherto unknown 6exo-substituted 2exo-norbornanols and their p-toluenesulfonates have been prepared by functionalization of intermediate norbornenes.
Die Synthese von 6exo-substituierten p-Toluolsulfonsaeure-estern
Fischer, Walter,Grob, Cyril A.,Sprecher, Georg von,Waldner, Adrian
, p. 816 - 823 (2007/10/02)
The preparation of hitherto unknown p-toluenesulfonates of 6exo-substituted 2endo-norbornanols is described.
