Chiral helicenoid diarylethene with highly diastereoselective photocyclization

A novel photochromic helicenoid diarylethene (R)-1-[1-(1-methoxymethoxyethyl)-2-naphtho[2,1-b]thienyl]-2-(2,4,5-trimethyl-3-thienyl)hexafluorocyclopentene was synthesized enantioselectively. It showed highly diastereoselective photocyclization (90% de) and a large change (950 degrees) in the specifi...

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Veröffentlicht in:	Journal of organic chemistry 2007-03, Vol.72 (5), p.1639-1644
Hauptverfasser:	TANI, Yutaka, UBUKATA, Takashi, YOKOYAMA, Yayoi, YOKOYAMA, Yasushi
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Photochemistry Physical chemistry of induced reactions (with radiations, particles and ultrasonics) Preparations and properties
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Beschreibung
Zusammenfassung:	A novel photochromic helicenoid diarylethene (R)-1-[1-(1-methoxymethoxyethyl)-2-naphtho[2,1-b]thienyl]-2-(2,4,5-trimethyl-3-thienyl)hexafluorocyclopentene was synthesized enantioselectively. It showed highly diastereoselective photocyclization (90% de) and a large change (950 degrees) in the specific optical rotation value at 633 nm upon UV light irradiation in ethyl acetate.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo062022v