Home / Publications / Synthesis of 1-iodo-1,2,3,4,4a,9a-hexahydrocarbazole, 2a,3,4,5,5a,10a-hexahydrooxazolocarbazolium iodide and 4-bromo-1,2,3,4,4a,11b-hexahydrodibenzoxazepine from N-benzoyl-2-(cyclohex-2-en-1-yl)aniline

Synthesis of 1-iodo-1,2,3,4,4a,9a-hexahydrocarbazole, 2a,3,4,5,5a,10a-hexahydrooxazolocarbazolium iodide and 4-bromo-1,2,3,4,4a,11b-hexahydrodibenzoxazepine from N-benzoyl-2-(cyclohex-2-en-1-yl)aniline

Rail Rafkatovich Gataullin ¹

Rail Rafkatovich Gataullin

Razida Ramirovna Ishberdina ¹

Razida Ramirovna Ishberdina

Olga Vladimirovna Shitikova ¹

Olga Vladimirovna Shitikova

Leonid Vasilevich Spirikhin ¹

Leonid Vasilevich Spirikhin

Tat'jana Vladimirovna Kazhanova ¹

Tat'jana Vladimirovna Kazhanova

Ildus Barievich Abdrakhmanov ¹

Ildus Barievich Abdrakhmanov

¹ Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation

10.1070/MC2004v014n05ABEH001924

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Published 2004-09-29

Communication , Volume 14, Issue 5, 219-221

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Gataullin R. R. et al. Synthesis of 1-iodo-1,2,3,4,4a,9a-hexahydrocarbazole, 2a,3,4,5,5a,10a-hexahydrooxazolocarbazolium iodide and 4-bromo-1,2,3,4,4a,11b-hexahydrodibenzoxazepine from N-benzoyl-2-(cyclohex-2-en-1-yl)aniline // Mendeleev Communications. 2004. Vol. 14. No. 5. pp. 219-221.

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Gataullin R. R., Ishberdina R. R., Shitikova O. V., Spirikhin L. V., Kazhanova T. V., Abdrakhmanov I. B. Synthesis of 1-iodo-1,2,3,4,4a,9a-hexahydrocarbazole, 2a,3,4,5,5a,10a-hexahydrooxazolocarbazolium iodide and 4-bromo-1,2,3,4,4a,11b-hexahydrodibenzoxazepine from N-benzoyl-2-(cyclohex-2-en-1-yl)aniline // Mendeleev Communications. 2004. Vol. 14. No. 5. pp. 219-221.

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TY - JOUR

DO - 10.1070/MC2004v014n05ABEH001924

UR - https://mendcomm.colab.ws/publications/10.1070/MC2004v014n05ABEH001924

TI - Synthesis of 1-iodo-1,2,3,4,4a,9a-hexahydrocarbazole, 2a,3,4,5,5a,10a-hexahydrooxazolocarbazolium iodide and 4-bromo-1,2,3,4,4a,11b-hexahydrodibenzoxazepine from N-benzoyl-2-(cyclohex-2-en-1-yl)aniline

T2 - Mendeleev Communications

AU - Gataullin, Rail Rafkatovich

AU - Ishberdina, Razida Ramirovna

AU - Shitikova, Olga Vladimirovna

AU - Spirikhin, Leonid Vasilevich

AU - Kazhanova, Tat'jana Vladimirovna

AU - Abdrakhmanov, Ildus Barievich

PY - 2004

DA - 2004/09/29

PB - Mendeleev Communications

SP - 219-221

IS - 5

VL - 14

ER -

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@article{2004_Gataullin,

author = {Rail Rafkatovich Gataullin and Razida Ramirovna Ishberdina and Olga Vladimirovna Shitikova and Leonid Vasilevich Spirikhin and Tat'jana Vladimirovna Kazhanova and Ildus Barievich Abdrakhmanov},

title = {Synthesis of 1-iodo-1,2,3,4,4a,9a-hexahydrocarbazole, 2a,3,4,5,5a,10a-hexahydrooxazolocarbazolium iodide and 4-bromo-1,2,3,4,4a,11b-hexahydrodibenzoxazepine from N-benzoyl-2-(cyclohex-2-en-1-yl)aniline},

journal = {Mendeleev Communications},

year = {2004},

volume = {14},

publisher = {Mendeleev Communications},

month = {Sep},

url = {https://mendcomm.colab.ws/publications/10.1070/MC2004v014n05ABEH001924},

number = {5},

pages = {219--221},

doi = {10.1070/MC2004v014n05ABEH001924}

}

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Gataullin, Rail Rafkatovich, et al. “Synthesis of 1-iodo-1,2,3,4,4a,9a-hexahydrocarbazole, 2a,3,4,5,5a,10a-hexahydrooxazolocarbazolium iodide and 4-bromo-1,2,3,4,4a,11b-hexahydrodibenzoxazepine from N-benzoyl-2-(cyclohex-2-en-1-yl)aniline.” Mendeleev Communications, vol. 14, no. 5, Sep. 2004, pp. 219-221. https://mendcomm.colab.ws/publications/10.1070/MC2004v014n05ABEH001924.

Abstract

The reaction of N-benzoyl-2-(cyclohex-2-en-1-yl)aniline 1 with molecular oxygen in the presence of NaHCO₃ results in N-benzoyl-1-iodo-1,2,3,4,4a,9a-hexahydrocarbazole, which was isomerised to 1-phenyl-2a,3,4,5,5a,10a-hexahydro[1,3]oxazolo-[5,4,3-j,k]carbazol-10-ium iodide, whereas the reaction of amide 1 with molecular bromine results in dibromide, but the interaction with NBS leads to 4-bromo-6-phenyl-1,2,3,4,4a,11b-hexahydrodibenzo[d,f][1,3] oxazepine.