Acid-catalyzed reaction of the steroidal Δ 1 -unsaturated 3β,5β- epoxyimino compound 2 and Δ 3 -unsaturated 1β,5β-epoxyimino products 3 and 7, results in intramolecular rearrangement involving the N-CH 3 group to give the corresponding perhydro-3,1-oxazine derivatives 9-11. Under similar reaction conditions, the saturated analogues 4, 6 and 8 remain unchanged. The difference in reactivity between the unsaturated and saturated compounds is studied and elucidated by the semiempirical molecular orbital MNDO-PM3 method.
TY - JOUR
AU - Rajković, Milica M.
AU - Lorenc, Ljubinka B.
AU - Juranić, Ivan
AU - Vitnik, Željko
AU - Mihailovíć, Milhailo Lj.
PY - 1999
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4391
AB - Acid-catalyzed reaction of the steroidal Δ 1 -unsaturated 3β,5β- epoxyimino compound 2 and Δ 3 -unsaturated 1β,5β-epoxyimino products 3 and 7, results in intramolecular rearrangement involving the N-CH 3 group to give the corresponding perhydro-3,1-oxazine derivatives 9-11. Under similar reaction conditions, the saturated analogues 4, 6 and 8 remain unchanged. The difference in reactivity between the unsaturated and saturated compounds is studied and elucidated by the semiempirical molecular orbital MNDO-PM3 method.
PB - Elsevier
T2 - Tetrahedron
T1 - Acid-catalyzed rearrangement of some steroidal isoxazolidines
VL - 55
IS - 21
SP - 6681
EP - 6690
DO - 10.1016/S0040-4020(99)00314-2
ER -
@article{
author = "Rajković, Milica M. and Lorenc, Ljubinka B. and Juranić, Ivan and Vitnik, Željko and Mihailovíć, Milhailo Lj.",
year = "1999",
url = "https://cer.ihtm.bg.ac.rs/handle/123456789/4391",
abstract = "Acid-catalyzed reaction of the steroidal Δ 1 -unsaturated 3β,5β- epoxyimino compound 2 and Δ 3 -unsaturated 1β,5β-epoxyimino products 3 and 7, results in intramolecular rearrangement involving the N-CH 3 group to give the corresponding perhydro-3,1-oxazine derivatives 9-11. Under similar reaction conditions, the saturated analogues 4, 6 and 8 remain unchanged. The difference in reactivity between the unsaturated and saturated compounds is studied and elucidated by the semiempirical molecular orbital MNDO-PM3 method.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Acid-catalyzed rearrangement of some steroidal isoxazolidines",
volume = "55",
number = "21",
pages = "6681-6690",
doi = "10.1016/S0040-4020(99)00314-2"
}
Rajković, M. M., Lorenc, L. B., Juranić, I., Vitnik, Ž.,& Mihailovíć, M. Lj. (1999). Acid-catalyzed rearrangement of some steroidal isoxazolidines.
Tetrahedron
Elsevier., 55(21), 6681-6690.
https://doi.org/10.1016/S0040-4020(99)00314-2
Rajković MM, Lorenc LB, Juranić I, Vitnik Ž, Mihailovíć ML. Acid-catalyzed rearrangement of some steroidal isoxazolidines. Tetrahedron. 1999;55(21):6681-6690
Rajković Milica M., Lorenc Ljubinka B., Juranić Ivan, Vitnik Željko, Mihailovíć Milhailo Lj., "Acid-catalyzed rearrangement of some steroidal isoxazolidines" Tetrahedron, 55, no. 21 (1999):6681-6690,
https://doi.org/10.1016/S0040-4020(99)00314-2 .
