Thiiranation of 2′-adamantylidene-9-benzonorbornenylidene using 4,4′-oligothiodimorpholine and brønsted acid

Autor: Yoshiaki Sugihara, Hiroko Nozumi, Juzo Nakayama
Rok vydání: 2009
Předmět:
Zdroj: Heteroatom Chemistry. 20:12-18
ISSN: 1098-1071
1042-7163
Popis: On leaving 4,4′-dithiodimorpholine 6 powder undisturbed at room temperature over 10 years, it led to the formation of 4,4′-tetrathiodimorpholine 7. Reactions of 2′-adamantylidene-9-benzonorbornenyidene 1 with 6, 7, and 4,4′-thiodimorpholine 8 and a Bronsted acid in CH2Cl2 at room temperature proceeded to afford the corresponding thiiranes, 2 and 3. The order of reactivity of 4,4′-oligothiodimorpholines combined with a Bronsted acid is 7 > 6 > 8. The thiirane 3 was transformed to 1 and 2 under the reaction conditions. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:12–18, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20505
Databáze: OpenAIRE