Literature DB >> 16599631

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

Salvatore D Lepore1, Anjan K Bhunia, Deboprosad Mondal, Pamela C Cohn, Craig Lefkowitz.   

Abstract

Arylsulfonates of hindered secondary alcohols are converted to the corresponding alkyl chlorides very rapidly and in good yields in the presence of titanium tetrachloride at low temperatures. These reactions proceed with exclusive retention of configuration.

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Year:  2006        PMID： 16599631      PMCID： PMC2527058          DOI： 10.1021/jo052333q

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 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.  Size-selective catalysis of ester and anilide cleavage by the dinuclear barium(II) complexes of cis- and trans-stilbenobis(18-crown-6).

Authors:  Roberta Cacciapaglia; Stefano Di Stefano; Luigi Mandolini
Journal:  J Org Chem       Date:  2002-01-25       Impact factor: 4.354

3.  Stereochemistry of oxachlorocarbene S(N)i reactions.

Authors:  Robert A Moss; Xiaolin Fu; Jingzhi Tian; Ronald Sauers; Peter Wipf
Journal:  Org Lett       Date:  2005-03-31       Impact factor: 6.005

4.  Indium-catalyzed direct chlorination of alcohols using chlorodimethylsilane-benzil as a selective and mild system.

Authors:  Makoto Yasuda; Satoshi Yamasaki; Yoshiyuki Onishi; Akio Baba
Journal:  J Am Chem Soc       Date:  2004-06-16       Impact factor: 15.419
  4 in total
  6 in total

1.  Recent advances in heterolytic nucleofugal leaving groups.

Authors:  Salvatore D Lepore; Deboprosad Mondal
Journal:  Tetrahedron       Date:  2007-06-11       Impact factor: 2.457

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.  Crown Ether Nucleophilic Catalysts (CENCs): Agents for Enhanced Silicon Radiofluorination.

Authors:  Susovan Jana; Mohammed H Al-Huniti; Bo Yeun Yang; Shuiyu Lu; Victor W Pike; Salvatore D Lepore
Journal:  J Org Chem       Date:  2017-02-20       Impact factor: 4.354

4.  Enhanced Nucleophilic Fluorination and Radiofluorination of Organosilanes Appended with Potassium-Chelating Leaving Groups.

Authors:  Mohammed H Al-Huniti; Shuiyu Lu; Victor W Pike; Salvatore D Lepore
Journal:  J Fluor Chem       Date:  2014-02-01       Impact factor: 2.050

5.  Nucleophile assisting leaving groups: a strategy for aliphatic 18F-fluorination.

Authors:  Shuiyu Lu; Salvatore D Lepore; Song Ye Li; Deboprosad Mondal; Pamela C Cohn; Anjan K Bhunia; Victor W Pike
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

6.  A Direct and Stereoretentive Synthesis of Amides from Cyclic Alcohols.

Authors:  Deboprosad Mondal; Luca Bellucci; Salvatore D Lepore
Journal:  European J Org Chem       Date:  2011-12
  6 in total

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