Journal
TETRAHEDRON LETTERS
Volume 58, Issue 40, Pages 3854-3858Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2017.08.061
Keywords
Naphthalenophanedienes; Benzyne Stevens rearrangement; Pseudo-geminal diastereomers; Pseudo-meta diastereomers; Ring strain
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Funding
- Ministry of Science and Technology - Taiwan
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Tetraoctyloxy-substituted naphthalenophanedienes were synthesized from tetraoctyloxy-substituted dithia[3.3]naphthalenophanes via sequential benzyne Stevens rearrangement, oxidation, and pyrolysis reactions. Surprisingly, only the pseudo-geminal isomer of tetraoctyloxy-substituted dithia[3.3]naphthalenophane was obtained after cyclization of the corresponding starting materials. The structures of the pseudo-geminal isomers of tetraoctyloxy-substituted dithia[3.3]naphthalenophane and tetraoctyloxy-substituted naphthalenophanediene were fully determined by nuclear magnetic resonance spectroscopy, high resolution mass spectrometry, and X-ray crystallography. The pseudo-geminal and pseudo-meta diastereomers of tetraoctyloxy-substituted naphthalenophanedienes were isolated by multiple fractional recrystallization from hexane at 5 degrees C. The solid state structure of the pseudo-geminal isomer of tetraoctyloxy-substituted naphthalenophanediene revealed strongly distorted naphthyl rings with high levels of ring strain. (C) 2017 Elsevier Ltd. All rights reserved.
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