Synthesis of Biphenanthrenyls and Role of C−H···X Noncovalent Interactions in Conformational Control | Zendy

Sharon Ashoke | Zendy; Maulik Prakas R. | Zendy; Vithana Champika | Zendy; Ohashi Yuji | Zendy; Ram Vishnu Ji | Zendy

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Synthesis of Biphenanthrenyls and Role of C−H···X Noncovalent Interactions in Conformational Control

Author(s) -

Sharon Ashoke,

Maulik Prakas R.,

Vithana Champika,

Ohashi Yuji,

Ram Vishnu Ji

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200300549

Subject(s) - chemistry , carbanion , ring (chemistry) , stereochemistry , non covalent interactions , pyran , crystal structure , crystallography , molecule , organic chemistry , hydrogen bond

A convenient synthesis of the 1,2′‐biphenanthrenyls 4a − c,f , 1,3′‐biphenanthrenyls 4d,e , thiabiphenanthrenyl 4g , the benzo[ h ]chromen‐2‐ylideneacetonitrile 5a and the methyl benzo[ h ]chromen‐2‐ylideneacetate 5b through carbanion‐induced ring transformation of 2 H ‐pyran‐2‐ones 1 or 2 and the 1‐naphthalenone 3a or thiochroman‐4‐one 3b separately is described. The structures of the biphenanthrenyls 4b and 4c have been confirmed by single‐crystal X‐ray diffraction. The conformations of 2b , 4b , 4c and 6 have also been studied to establish the role of C−H ··· X interaction in conformational control. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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