Literature DB >> 15787509

Stereochemistry of oxachlorocarbene S(N)i reactions.

Robert A Moss1, Xiaolin Fu, Jingzhi Tian, Ronald Sauers, Peter Wipf.   

Abstract

[reaction: see text] 3-Nortricyclyloxychlorocarbene and trans-4-methylcyclohexyloxychlorocarbene both fragment in hydrocarbon solvents with extensive loss of stereochemical integrity to the corresponding chlorides via competitive and nearly isoenergetic S(N)i-like transition states.

Entities:  

Year:  2005        PMID： 15787509     DOI： 10.1021/ol050185k

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  Arylsulfonate-based nucleophile assisting leaving groups.

Authors:  Salvatore D Lepore; Anjan K Bhunia; Pamela Cohn
Journal:  J Org Chem       Date:  2005-09-30       Impact factor: 4.354

2.  Stereoretentive chlorination of cyclic alcohols catalyzed by titanium(IV) tetrachloride: evidence for a front side attack mechanism.

Authors:  Deboprosad Mondal; Song Ye Li; Luca Bellucci; Teodoro Laino; Andrea Tafi; Salvatore Guccione; Salvatore D Lepore
Journal:  J Org Chem       Date:  2013-01-23       Impact factor: 4.354

3.  Rapid conversion of hindered arylsulfonates to alkyl chlorides with retention of configuration.

Authors:  Salvatore D Lepore; Anjan K Bhunia; Deboprosad Mondal; Pamela C Cohn; Craig Lefkowitz
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354
  3 in total

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