Dataset Information

1-Methyl-2,6-cis-distyrylpiperidine.

ABSTRACT: The complete molecule of the title compound, C(22)H(25)N, is generated by crystallographic mirror symmetry, with two C atoms and the N atom lying on the mirror plane. The central ring adopts a chair conformation and the dihedral angle between the aromatic rings is 56.69?(4)°.

SUBMITTER: Zheng G

PROVIDER: S-EPMC2980188 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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Publications

1-Methyl-2,6-cis-distyrylpiperidine.

Zheng Guangrong G Parkin Sean S Dwoskin Linda P LP Crooks Peter A PA

Acta crystallographica. Section E, Structure reports online 20091209 Pt 1

The complete molecule of the title compound, C(22)H(25)N, is generated by crystallographic mirror symmetry, with two C atoms and the N atom lying on the mirror plane. The central ring adopts a chair conformation and the dihedral angle between the aromatic rings is 56.69 (4)°. ...[more]

PMID: 21580176

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Project description:Most recent advances in metallation chemistry have centred on the bulky secondary amide 2,2,6,6-tetramethylpiperidide (TMP) within mixed metal, often ate, compositions. However, the precursor amine TMP(H) is rather expensive so a cheaper substitute would be welcome. Thus this study was aimed towards developing cheaper non-TMP based mixed-metal bases and, as cis-2,6-dimethylpiperidide (cis-DMP) was chosen as the alternative amide, developing cis-DMP zincate chemistry which has received meagre attention compared to that of its methyl-rich counterpart TMP. A new lithium diethylzincate, [(TMEDA)LiZn(cis-DMP)Et2] (TMEDA=N,N,N',N'-tetramethylethylenediamine) has been synthesised by co-complexation of Li(cis-DMP), Et2Zn and TMEDA, and characterised by NMR (including DOSY) spectroscopy and X-ray crystallography, which revealed a dinuclear contact ion pair arrangement. By using N,N-diisopropylbenzamide as a test aromatic substrate, the deprotonative reactivity of [(TMEDA)LiZn(cis-DMP)Et2] has been probed and contrasted with that of the known but previously uninvestigated di-tert-butylzincate, [(TMEDA)LiZn(cis-DMP)tBu2]. The former was found to be the superior base (for example, producing the ortho-deuteriated product in respective yields of 78% and 48% following D2O quenching of zincated benzamide intermediates). An 88% yield of 2-iodo-N,N-diisopropylbenzamide was obtained on reaction of two equivalents of the diethylzincate with the benzamide followed by iodination. Comparisons are also drawn using 1,1,1,3,3,3-hexamethyldisilazide (HMDS), diisopropylamide and TMP as the amide component in the lithium amide, Et2Zn and TMEDA system. Under certain conditions, the cis-DMP base system was found to give improved results in comparison to HMDS and diisopropylamide (DA), and comparable results to a TMP system. Two novel complexes isolated from reactions of the di-tert-butylzincate and crystallographically characterised, namely the pre-metallation complex [{(iPr)2N(Ph)C=O}LiZn(cis-DMP)tBu2] and the post-metallation complex [(TMEDA)Li(cis-DMP){2-[1-C(=O)N(iPr)2]C6H4}Zn(tBu)], shed valuable light on the structures and mechanisms involved in these alkali-metal-mediated zincation reactions. Aspects of these reactions are also modelled by DFT calculations.

Dataset Information

1-Methyl-2,6-cis-distyrylpiperidine.

Publications

1-Methyl-2,6-cis-distyrylpiperidine.

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