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Keywords = diazecine

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18 pages, 3809 KiB  
Article
Synthesis, Structure, and Reactivity of Binaphthyl Supported Dihydro[1,6]diazecines
by Miran Lemmerer, Michael Abraham, Bogdan R. Brutiu, Alexander Roller and Michael Widhalm
Molecules 2019, 24(17), 3098; https://doi.org/10.3390/molecules24173098 - 26 Aug 2019
Viewed by 3888
Abstract
A short approach to chiral diaza-olefines from protected 2,2′-diamino-1,1′-binaphthyl is presented. Cis- and trans-olefines can be selectively obtained by twofold N-allylation followed by RCM or by bridging a 2,2′-diamino-1,1′-binaphthyl precursor with trans-1,4-dibromo-2-butene. Deprotection afforded cis- and trans-dihydro[1,6]diazecines [...] Read more.
A short approach to chiral diaza-olefines from protected 2,2′-diamino-1,1′-binaphthyl is presented. Cis- and trans-olefines can be selectively obtained by twofold N-allylation followed by RCM or by bridging a 2,2′-diamino-1,1′-binaphthyl precursor with trans-1,4-dibromo-2-butene. Deprotection afforded cis- and trans-dihydro[1,6]diazecines 1 in 58 and 64% overall yield. The reactivity of the but-2-ene-1,4-diyl fragment was investigated yielding corresponding epoxides, diols, and mono- and dibromo products. In several cases rearrangements and participation of the proximate N-Boc group was observed. In no case could allylic substitution be accomplished. From 13 compounds X-ray structure analyses could be obtained. Full article
(This article belongs to the Special Issue Non-Natural Multi-Heteroatom Heterocycles: New Chemical Space)
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9 pages, 495 KiB  
Article
Fluoride Ion as Ligand and Hydrogen Bond Acceptor: Crystal Structures of Two Dinuclear CuII Complexes Built on a Diazecine Template
by Juan Olguín, Sylvain Bernès and Laura Gasque
Crystals 2012, 2(3), 1357-1365; https://doi.org/10.3390/cryst2031357 - 18 Sep 2012
Cited by 5 | Viewed by 7030
Abstract
Two dinuclear CuII complexes based on a diazecine ligand were characterized by X-ray diffraction, one of which includes the rare CuII–F bond, resulting from dissociation of a BF4 ion. The F ligands actively participate in the crystal [...] Read more.
Two dinuclear CuII complexes based on a diazecine ligand were characterized by X-ray diffraction, one of which includes the rare CuII–F bond, resulting from dissociation of a BF4 ion. The F ligands actively participate in the crystal structure, behaving as acceptors for hydrogen bonding. Full article
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