1,1‐ and 1, o ‐Dilithioallyl Phenyl Sulfone: Synthesis, Geminal Cycloalkylation, and Lithium‐Titanium Exchange | Zendy

Vollhardt Jürgen | Zendy; Gais HansJoachim | Zendy; Lukas Karl L. | Zendy

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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 .

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