TY  - JOUR
AU  - Yucel, Baris
AU  - Valentić, Nataša
AU  - Noltemeyer, Mathias
AU  - De Meijere, Armin
PY  - 2007
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5481
AB  - A palladium-catalyzed reaction of methylenespiropentane (11) with iodobenzene (12) under typical Heck conditions [Pd(OAc)2, PPh 3, Et3N, DMF] produced a mixture of the unstable [3]dendralene 13 and allylidenecyclopropane 14 in 38 % yield. When an analogous reaction with iodobenzene was carried out in the presence of morpholine (25) and of tris(2-furyl)phosphane (TFP) instead of triphenylphosphane, the dienes 26, 28 and 31 were generated by nucleophilic trapping of π-allylpalladium intermediates 30 and 32. The cross coupling of methylenespiropentane (11) with the functionalized aryl iodides 33a-g in the presence of a palladium precatalyst [Pd(OAc)2, TFP, Et3N, DMF] at 80°C, 3 h, provided the seven-membered 3,4-dimethylene-substituted heterocycles 34a-g and 35b which, upon addition of dimethyl fumarate (19), underwent Diels-Alder reactions to furnish bicyclic and higher oligocyclic dihydrobenzoxepine and -benzazepine derivatives 36a-g and 37b, yet in rather moderate yields of 18-29% only. The overall process constitutes a one-pot, two-step, three-component queuing cascade.
PB  - Wiley-Blackwell
T2  - European Journal of Organic Chemistry
T1  - A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives
EP  - 4090
SP  - 4081
VL  - 24
DO  - 10.1002/ejoc.200700354
ER  - 

@article{
author = "Yucel, Baris and Valentić, Nataša and Noltemeyer, Mathias and De Meijere, Armin",
year = "2007",
abstract = "A palladium-catalyzed reaction of methylenespiropentane (11) with iodobenzene (12) under typical Heck conditions [Pd(OAc)2, PPh 3, Et3N, DMF] produced a mixture of the unstable [3]dendralene 13 and allylidenecyclopropane 14 in 38 % yield. When an analogous reaction with iodobenzene was carried out in the presence of morpholine (25) and of tris(2-furyl)phosphane (TFP) instead of triphenylphosphane, the dienes 26, 28 and 31 were generated by nucleophilic trapping of π-allylpalladium intermediates 30 and 32. The cross coupling of methylenespiropentane (11) with the functionalized aryl iodides 33a-g in the presence of a palladium precatalyst [Pd(OAc)2, TFP, Et3N, DMF] at 80°C, 3 h, provided the seven-membered 3,4-dimethylene-substituted heterocycles 34a-g and 35b which, upon addition of dimethyl fumarate (19), underwent Diels-Alder reactions to furnish bicyclic and higher oligocyclic dihydrobenzoxepine and -benzazepine derivatives 36a-g and 37b, yet in rather moderate yields of 18-29% only. The overall process constitutes a one-pot, two-step, three-component queuing cascade.",
publisher = "Wiley-Blackwell",
journal = "European Journal of Organic Chemistry",
title = "A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives",
pages = "4090-4081",
volume = "24",
doi = "10.1002/ejoc.200700354"
}

Yucel, B., Valentić, N., Noltemeyer, M.,& De Meijere, A.. (2007). A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives. in European Journal of Organic Chemistry
Wiley-Blackwell., 24, 4081-4090.
https://doi.org/10.1002/ejoc.200700354

Yucel B, Valentić N, Noltemeyer M, De Meijere A. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives. in European Journal of Organic Chemistry. 2007;24:4081-4090.
doi:10.1002/ejoc.200700354 .

Yucel, Baris, Valentić, Nataša, Noltemeyer, Mathias, De Meijere, Armin, "A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives" in European Journal of Organic Chemistry, 24 (2007):4081-4090,
https://doi.org/10.1002/ejoc.200700354 . .

TY  - JOUR
AU  - Yucel, Baris
AU  - Valentić, Nataša
AU  - Noltemeyer, Mathias
AU  - de Meijere, Armin
PY  - 2007
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1171
AB  - A palladium-catalyzed reaction of methylenespiropentane (11) with iodobenzene (12) under typical Heck conditions [Pd(OAC)(2), PPh3, Et3N, DMF] produced a mixture of the unstable [3]dendralene 13 and allylidenecyclopropane 14 in 38 % yield. When an analogous reaction with iodobenzene was carried out in the presence of morpholine (25) and of tris(2-furyl)phosphane (TFP) instead of triphenylphosphane, the dienes 26, 28 and 31 were generated by nucleophilic trapping of pi-allylpalladium intermediates 30 and 32. The cross coupling of methylenespiropentane (11) with the functionalized aryl iodides 33a-g in the presence of a palladium precatalyst [Pd(OAc)2, TFP, Et3N, DMF] at 80 degrees C, 3 h, provided the seven-membered 3,4-dimethylene-substituted heterocycles 34a-g and 35b which, upon addition of dimethyl fumarate (19), underwent Diels-Alder reactions to furnish bicyclic and higher oligocyclic dihydrobenzoxepine and -benzazepine derivatives 36a-g and 37b, yet in rather moderate yields of 18-29 % only. The overall process constitutes a one-pot, two-step, three-component queuing cascade. (
PB  - Wiley-VCH Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - Cyclopropyl building blocks in organic synthesis, part 143. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives
EP  - 4090
IS  - 24
SP  - 4081
VL  - 2007
DO  - 10.1002/ejoc.200700354
ER  - 

@article{
author = "Yucel, Baris and Valentić, Nataša and Noltemeyer, Mathias and de Meijere, Armin",
year = "2007",
abstract = "A palladium-catalyzed reaction of methylenespiropentane (11) with iodobenzene (12) under typical Heck conditions [Pd(OAC)(2), PPh3, Et3N, DMF] produced a mixture of the unstable [3]dendralene 13 and allylidenecyclopropane 14 in 38 % yield. When an analogous reaction with iodobenzene was carried out in the presence of morpholine (25) and of tris(2-furyl)phosphane (TFP) instead of triphenylphosphane, the dienes 26, 28 and 31 were generated by nucleophilic trapping of pi-allylpalladium intermediates 30 and 32. The cross coupling of methylenespiropentane (11) with the functionalized aryl iodides 33a-g in the presence of a palladium precatalyst [Pd(OAc)2, TFP, Et3N, DMF] at 80 degrees C, 3 h, provided the seven-membered 3,4-dimethylene-substituted heterocycles 34a-g and 35b which, upon addition of dimethyl fumarate (19), underwent Diels-Alder reactions to furnish bicyclic and higher oligocyclic dihydrobenzoxepine and -benzazepine derivatives 36a-g and 37b, yet in rather moderate yields of 18-29 % only. The overall process constitutes a one-pot, two-step, three-component queuing cascade. (",
publisher = "Wiley-VCH Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Cyclopropyl building blocks in organic synthesis, part 143. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives",
pages = "4090-4081",
number = "24",
volume = "2007",
doi = "10.1002/ejoc.200700354"
}

Yucel, B., Valentić, N., Noltemeyer, M.,& de Meijere, A.. (2007). Cyclopropyl building blocks in organic synthesis, part 143. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives. in European Journal of Organic Chemistry
Wiley-VCH Verlag Gmbh, Weinheim., 2007(24), 4081-4090.
https://doi.org/10.1002/ejoc.200700354

Yucel B, Valentić N, Noltemeyer M, de Meijere A. Cyclopropyl building blocks in organic synthesis, part 143. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives. in European Journal of Organic Chemistry. 2007;2007(24):4081-4090.
doi:10.1002/ejoc.200700354 .

Yucel, Baris, Valentić, Nataša, Noltemeyer, Mathias, de Meijere, Armin, "Cyclopropyl building blocks in organic synthesis, part 143. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives" in European Journal of Organic Chemistry, 2007, no. 24 (2007):4081-4090,
https://doi.org/10.1002/ejoc.200700354 . .

TY  - JOUR
AU  - Valentić, Nataša
AU  - Vitnik, Željko
AU  - Kozhushkov, Sergei I.
AU  - de Meijere, Armin
AU  - Ušćumlić, Gordana
AU  - Juranić, Ivan
PY  - 2005
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/823
AB  - Linear free energy relationships (LFER) were applied to the H-1 and C-13 NMR chemical shifts (delta(N), N=H-1 and C-13, respectively) in the unsaturated backbone of cross-conjugated trienes 3-methylene-2-substituted-1,4-pentadienes. The NMR data were correlated using five different LFER models, based on the mono, the dual and the triple substituent parameter (MSP, DSP and TSP, respectively) treatment. The simple and extended Hammett equations, and the three postulated unconventional LFER models obtained by adaptation of the later, were used. The geometry data, which are needed in Karplus-type and McConnell-type analysis, were obtained using semi-empirical MNDO-PM3 calculations. In correlating the data the TSP approach was more successful than the MSP and DSP approaches. The fact that the calculated molecular geometries allow accurate prediction of the NMR data confirms the validity of unconventional LFER models used. These results suggest the s-cis conformation of the cross-conjugated triene as the preferred one. Postulated unconventional DSP and TSP equations enable the assessment of electronic substituent effects in the presence of other interfering influences.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Molecular Structure
T1  - Linear free energy relationships of the H-1 and C-13 NMR chemical shifts of 3-methylene-2-substituted-1,4-pentadienes
EP  - 908
SP  - 901
VL  - 744
DO  - 10.1016/j.molstruc.2004.12.014
ER  - 

@article{
author = "Valentić, Nataša and Vitnik, Željko and Kozhushkov, Sergei I. and de Meijere, Armin and Ušćumlić, Gordana and Juranić, Ivan",
year = "2005",
abstract = "Linear free energy relationships (LFER) were applied to the H-1 and C-13 NMR chemical shifts (delta(N), N=H-1 and C-13, respectively) in the unsaturated backbone of cross-conjugated trienes 3-methylene-2-substituted-1,4-pentadienes. The NMR data were correlated using five different LFER models, based on the mono, the dual and the triple substituent parameter (MSP, DSP and TSP, respectively) treatment. The simple and extended Hammett equations, and the three postulated unconventional LFER models obtained by adaptation of the later, were used. The geometry data, which are needed in Karplus-type and McConnell-type analysis, were obtained using semi-empirical MNDO-PM3 calculations. In correlating the data the TSP approach was more successful than the MSP and DSP approaches. The fact that the calculated molecular geometries allow accurate prediction of the NMR data confirms the validity of unconventional LFER models used. These results suggest the s-cis conformation of the cross-conjugated triene as the preferred one. Postulated unconventional DSP and TSP equations enable the assessment of electronic substituent effects in the presence of other interfering influences.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Molecular Structure",
title = "Linear free energy relationships of the H-1 and C-13 NMR chemical shifts of 3-methylene-2-substituted-1,4-pentadienes",
pages = "908-901",
volume = "744",
doi = "10.1016/j.molstruc.2004.12.014"
}

Valentić, N., Vitnik, Ž., Kozhushkov, S. I., de Meijere, A., Ušćumlić, G.,& Juranić, I.. (2005). Linear free energy relationships of the H-1 and C-13 NMR chemical shifts of 3-methylene-2-substituted-1,4-pentadienes. in Journal of Molecular Structure
Elsevier Science Bv, Amsterdam., 744, 901-908.
https://doi.org/10.1016/j.molstruc.2004.12.014

Valentić N, Vitnik Ž, Kozhushkov SI, de Meijere A, Ušćumlić G, Juranić I. Linear free energy relationships of the H-1 and C-13 NMR chemical shifts of 3-methylene-2-substituted-1,4-pentadienes. in Journal of Molecular Structure. 2005;744:901-908.
doi:10.1016/j.molstruc.2004.12.014 .

Valentić, Nataša, Vitnik, Željko, Kozhushkov, Sergei I., de Meijere, Armin, Ušćumlić, Gordana, Juranić, Ivan, "Linear free energy relationships of the H-1 and C-13 NMR chemical shifts of 3-methylene-2-substituted-1,4-pentadienes" in Journal of Molecular Structure, 744 (2005):901-908,
https://doi.org/10.1016/j.molstruc.2004.12.014 . .