Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates
Само за регистроване кориснике
1979
Чланак у часопису (Објављена верзија)
,
Elsevier
Метаподаци
Приказ свих података о документуАпстракт
The solvolysis of (Z)- and (E)-3β-acyloxy-5,10-seco-1(10)-cholesten-5β-ol p-nitrobenzoates 4 and 5 has been investigated and compared with the solvolytic reactivity of the epimeric (Z)- and (E)-5α-p-nitrobenzoates 1 and 2, as well as of the reference compound, i.e. the 1,10-saturated 5α-p-nitrobenzoate. Kinetic data and product analysis revealed that the relative spatial orientation of the 1(10)-olefinic double bond and the chiral center at C(5) in the 10-membered ring, which these secosteroidal 5-p-nitrobenzoates can adopt in the transition state, is the main factor which determines their solvolytic behaviour, so that the esters 1,2 and 5 solvolyse with transannular double bond participation, while such an interaction is not present in the case of the (Z)-5β-ester 4. © 1979.
Извор:
Tetrahedron, 1979, 35, 20, 2445-2452Издавач:
- Pergamon Press
Финансирање / пројекти:
- Serbian Republic Research Fund
- Serbian Academy of Science and Arts
Институција/група
IHTMTY - JOUR AU - Lorenc, Ljubinka AU - Gašić, Miroslav J. AU - Dabović, Milan AU - Vuletić, N AU - Mihailović, Milhailo Lj. PY - 1979 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2700 AB - The solvolysis of (Z)- and (E)-3β-acyloxy-5,10-seco-1(10)-cholesten-5β-ol p-nitrobenzoates 4 and 5 has been investigated and compared with the solvolytic reactivity of the epimeric (Z)- and (E)-5α-p-nitrobenzoates 1 and 2, as well as of the reference compound, i.e. the 1,10-saturated 5α-p-nitrobenzoate. Kinetic data and product analysis revealed that the relative spatial orientation of the 1(10)-olefinic double bond and the chiral center at C(5) in the 10-membered ring, which these secosteroidal 5-p-nitrobenzoates can adopt in the transition state, is the main factor which determines their solvolytic behaviour, so that the esters 1,2 and 5 solvolyse with transannular double bond participation, while such an interaction is not present in the case of the (Z)-5β-ester 4. © 1979. PB - Pergamon Press T2 - Tetrahedron T2 - Tetrahedron T1 - Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates VL - 35 IS - 20 SP - 2445 EP - 2452 DO - 10.1016/S0040-4020(01)93762-7 ER -
@article{ author = "Lorenc, Ljubinka and Gašić, Miroslav J. and Dabović, Milan and Vuletić, N and Mihailović, Milhailo Lj.", year = "1979", abstract = "The solvolysis of (Z)- and (E)-3β-acyloxy-5,10-seco-1(10)-cholesten-5β-ol p-nitrobenzoates 4 and 5 has been investigated and compared with the solvolytic reactivity of the epimeric (Z)- and (E)-5α-p-nitrobenzoates 1 and 2, as well as of the reference compound, i.e. the 1,10-saturated 5α-p-nitrobenzoate. Kinetic data and product analysis revealed that the relative spatial orientation of the 1(10)-olefinic double bond and the chiral center at C(5) in the 10-membered ring, which these secosteroidal 5-p-nitrobenzoates can adopt in the transition state, is the main factor which determines their solvolytic behaviour, so that the esters 1,2 and 5 solvolyse with transannular double bond participation, while such an interaction is not present in the case of the (Z)-5β-ester 4. © 1979.", publisher = "Pergamon Press", journal = "Tetrahedron, Tetrahedron", title = "Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates", volume = "35", number = "20", pages = "2445-2452", doi = "10.1016/S0040-4020(01)93762-7" }
Lorenc, L., Gašić, M. J., Dabović, M., Vuletić, N.,& Mihailović, M. Lj.. (1979). Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates. in Tetrahedron Pergamon Press., 35(20), 2445-2452. https://doi.org/10.1016/S0040-4020(01)93762-7
Lorenc L, Gašić MJ, Dabović M, Vuletić N, Mihailović ML. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates. in Tetrahedron. 1979;35(20):2445-2452. doi:10.1016/S0040-4020(01)93762-7 .
Lorenc, Ljubinka, Gašić, Miroslav J., Dabović, Milan, Vuletić, N, Mihailović, Milhailo Lj., "Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates" in Tetrahedron, 35, no. 20 (1979):2445-2452, https://doi.org/10.1016/S0040-4020(01)93762-7 . .