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Azo Bridges from Azines, XXIV. Tuning the Addition of Thiols to Parallel CC/NN Bonds from Transannular to Normal Addition

✍ Scribed by Hünig, Siegfried ;Brand, Uwe ;Peters, Karl ;Prokschy, Frank ;von Schnering, Hans Georg

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 535 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719970424

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✦ Synopsis

Abstract

As an example of system A, compound 5 was reacted with several thiols. A radical route procedures transannular 1,4‐addition products (6a/b). In the presence of sulfur, the addition reaction is strongly enhanced, and a polar route yields 1,2‐adducts (7a/b). Structures 6a/b and 7a/b are supported by X‐ray analysis. The different reaction modes are discussed.