NDLI: Stereo-selectivity in a cyclotriphosphazene derivative bearing an exocyclic P

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Yuksel, Fatma Eçik, Esra Tanriverdi Çiftçi, Gönül Yenilmez Davies, David B. Besli, Serap Kiliç, Adem
Description	Author Affiliation: Eçik ET ( Department of Chemistry, Gebze Institute of Technology, Gebze, Turkey. etanriverdi@gyte.edu.tr)
Abstract	Nucleophilic substitution reactions of $N_{3}P_{3}Cl_{4}[O(CH_{2})_{2}NCH_{3}],$ (1) with the sodium salts of mono- and di-functional alcohols [ methanol (2), phenol (3), tetraethyleneglycol (4) and 1,3-propanediol (5)] were carried out in order to investigate a possible directing effect of the spiro O-moiety on the formation of mono-substituted (2a, 3a), non-geminal di-substituted (2c, 3c) and ansa (4a, 5a) derivatives. Compounds isolated from the reactions were characterized by elemental analysis , mass spectrometry , $^{1}H$ and $^{31}P$ NMR spectroscopy and X-ray crystallographic analysis showed that the substituent OR in compounds (2a, 3a and 2c, 3c) and the ansa-ring in compounds (4a, 5a) formed cis to the P–O moiety of the exocyclic $[O(CH_{2})_{2}NCH_{3}]$ spiro ring. The formation of products (2a–d, 3a–d, 4a, 5a and 5b) was quantified from the $^{31}P$ NMR spectra of the reaction mixtures, which showed an overwhelming preference for derivatives (2a, 3a, 2c, 3c, 4a, 5a) with the substituent cis to the P–O moiety of the exocyclic spiro ring (2a, 3a, 2c, 3c, 4a, 5a), except for reaction with 1,3-propanediol where the six-membered ring spiro derivative (5b) was about three times more abundant than the eight-membered ring ansa-derivative (5a). Overwhelming formation of products with the substituent cis to the exocyclic P–O moiety is proof that the cation -assisted mechanism is responsible for the stereo-selectivity in the reactions with alkoxides.
ISSN	14779226
Issue Number	22
Journal	Dalton Trans.
Volume Number	41
e-ISSN	13645447
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2012-06-14
Publisher Place	Great Britain (UK)
Access Restriction	Subscribed
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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