TY  - 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 . .