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Selection of the Cis and Trans phosph(III)azane Macrocycles [{P(mu-NtBu)}2(1-Y-2-NH-C6H4)]2(Y=O, S)

Felipe Garcia, Jonathan M Goodman, Richard A Kowenicki, Mary McPartlin, Lucia Riera, Maria A Silva, Andreas Wirsing, Dominic S Wright

Dalton Trans. 2005 May 21;(10):1764-73.

PMID: 15877146

Abstract:

The 1 : 1 reactions of [ClP(mu-NtBu)]2 with the difunctional aromatic amines 1,2-1-YH-2-NH2-C6H4 in the presence of Et3N give the dimeric phosph(III)azane macrocycles [{P(mu-NtBu)2(1-Y-2-HN-C6H4)]2, predominantly as the cis isomer in the case of Y=O (1.cis) and as the trans isomer for Y=S (2.trans). Model M.O. calculations suggest that the selection of the cis and trans isomers is not thermodynamically controlled. The alternative isomers 1.trans and 2.cis are generated exclusively by the deprotonation of the model intermediates [(1-Y-2-NH2-C6H4)P(mu-NtBu)]2[Y=O (3), S (4)] with nBuLi followed by cyclisation with [ClP(mu-NtBu)]2. The solid-state structures of 1.cis/trans(50 : 50), 2.cis, 3 and 4 are reported.

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AP3879605 2-trans,6-cis-Farnesol 2-trans,6-cis-Farnesol 3879-60-5 Price
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