ISSN:
0009-2940
Keywords:
Amine-Diboroxanes, bicyclic
;
1,2-Deaminoboration, intramolecular
;
Deoxyboration
;
Allyl-aminoboranes, organosubstituted, rearrangement
;
C-Borylation
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Rearrangement and Degradation of Bicyclic Amine-Tetraalkyldiboroxanes[1]The amine-tetraalkyldiboroxanes [1a: R1,4,7,7′ = Et; 1b: R1,4,7 = Et, R7′ = Ph; 1b′: R4,7,7′ = Et,R1 = Ph; 1c: R1,7,7′ = Et, R4 = Ph] react on heating by EtBO elimination and allylborane rearrangement to yield the allyl-aminoboranes Me2NB(Et)CH2C(R4)=C(R7,7′) [2a: R4,7,7′ = Et; 2b/2b′: R4 = Et, R7,7′ = Et, Ph; 2c: R4 = Ph, R7,7′ = Et]: On heating above 60°C the diastereomeric syn/anti-Id/1d′(Id: R1,7 = C8H14, R4,7′ = Et; 1d′: R1,7′ = C8H14, R4,7 = Et) give the unsaturated rac-amino-trialkyldiboroxane (rac-3) (X-ray structure analysis) by intramolecular 1,2-deaminoboration. rac-3 is characterized by reaction with (Et2BH)2 and (Et2BD)2 with formation of the 1,2,6-oxadiborinane 5 by evolution of H2 or HD respectively. The intramolecular CH-borylation of rac-3 is compared with those of the thujopsen hydrocarbons I-III.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19941271005
