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1,1‐ and 1, o ‐Dilithioallyl Phenyl Sulfone: Synthesis, Geminal Cycloalkylation, and Lithium‐Titanium Exchange
Author(s) -
Vollhardt Jürgen,
Gais HansJoachim,
Lukas Karl L.
Publication year - 1985
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198506101
Subject(s) - sulfone , geminal , chemistry , lithium (medication) , derivative (finance) , medicinal chemistry , titanium , organic chemistry , medicine , financial economics , economics , endocrinology
Stepwise lithiation of allyl phenyl sulfone leads via the 1‐lithio‐ to the 1, o ‐dilithio‐derivative 1 , which isomerizes to the surprinsingly stable 1,1‐dilithio derivative 2 . The synthetic potential of 1 and 2 is exceptional. Thus, 2 reacts with ( i PrO) 2 TiCl 2 and carbonyl compounds R 1 R 2 CO with carbonyl olefination to give 3 and/or with addition to give 4 .