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Preparation and crystal structures of two 3-anthracenyl isoxazolyl sulfonamides

✍ Scribed by Chun Li; Brendan Twamley; Nicholas R. Natale

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
394 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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Lateral metalation and oxidation of 3‐(9′‐anthryl)‐isoxazoles (1), using Davis' oxaziridine (6), produced the desired hydroxylation (2), along with sulfonamide adduct (3), and in the case of the use of butyl lithium as base, butyl addition products (4) and (5). Structures of isoxazole sulfonamides (3a) and (5a), were obtained as the SR/RS‐diastereomer, however, studies indicate that this is a consequence of the crystallization process. Metalation studies with isoxazole (8) demonstrate that hydroxylation (9), can be carried out cleanly, minimizing formation of (10), using camphorsulfonyloxaziridine (7) as an electrophile.

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Preparation and crystal structures of tw
Preparation and crystal structures of two salts with the 5-nitrotetrazolate anion
✍ Thomas M. Klapötke; Carles Miró Sabaté; Jan M. Welch 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 381 KB

Tetraphenylphosphonium 5-nitrotetrazolate (2) was prepared by metathesis of sodium 5-nitrotetrazolate dihydrate (1; NaNT) with tetraphenylphosphonium chloride in acetone. The new compound was fully characterized by vibrational (IR, Raman) and NMR ( 1 H, 13 C, and 14 N) spectroscopies, elemental anal