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Azo Bridges from Azines, XXIV . Tuning the Addition of Thiols to Parallel CC/NN Bonds from Transannular to Normal Addition
Author(s) -
Hünig Siegfried,
Brand Uwe,
Peters Karl,
Prokschy Frank,
von Schnering Hans Georg
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970424
Subject(s) - chemistry , adduct , sulfur , polar , addition reaction , medicinal chemistry , combinatorial chemistry , stereochemistry , computational chemistry , organic chemistry , catalysis , physics , astronomy
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.