Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of .gamma.-cyclodextrin

0482139 - ÚMCH 2018 RIV DE eng J - Journal Article
Bláhová, M. - Filippov, Sergey K. - Kováčik, L. - Horský, Jiří - Hybelbauerová, S. - Syrová, Z. - Křížek, T. - Jindřich, J.
Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of .gamma.-cyclodextrin.
Beilstein Journal of Organic Chemistry. Roč. 13, 27 November (2017), s. 2509-2520. ISSN 1860-5397. E-ISSN 1860-5397
R&D Projects: GA ČR(CZ) GA17-07164S; GA MŠMT(CZ) 7F14009
Institutional support: RVO:61389013
Keywords : gamma-cyclodextrin * naphthylallyl derivatives * regioselective alkylation
OECD category: Polymer science
Impact factor: 2.330, year: 2017

Monosubstituted derivatives of gamma-cyclodextrin (gamma-CD) are suitable building blocks for supramolecular polymers, and can also serve as precursors for the synthesis of other regioselectively monosubstituted gamma-CD derivatives. We prepared a set of monosubstituted 2I-O-, 3I-O-, and 6I-O-(3-(naphthalen-2-yl)prop-2-en-1-yl) derivatives of gamma-CD using two different methods. A key step of the first synthetic procedure is a cross-metathesis between previously described regioisomers of mono-O-allyl derivatives of gamma-CD and 2-vinylnaphthalene which gives yields of about 16-25% (2-5% starting from gamma-CD). To increase the overall yields, we have developed another method, based on a direct alkylation of gamma-CD with 3-(naphthalen-2-yl)allyl chloride as the alkylating reagent. Highly regioselective reaction conditions, which differ for each regioisomer in a used base, gave the monosubstituted isomers in yields between 12-19%. Supramolecular properties of these derivatives were studied by DLS, ITC, NMR, and Cryo-TEM.
Permanent Link: http://hdl.handle.net/11104/0278617