Facile synthetic approaches to 1-thiocyclopropanecarboxylates. (3rd July 2017)
- Record Type:
- Journal Article
- Title:
- Facile synthetic approaches to 1-thiocyclopropanecarboxylates. (3rd July 2017)
- Main Title:
- Facile synthetic approaches to 1-thiocyclopropanecarboxylates
- Authors:
- Zhang, Xiansheng
Wu, Jingwei
Liu, Yuqiang
Xie, Yafei
Liu, Changying
Wang, Jianwu
Zhao, Guilong - Abstract:
- GRAPHICAL ABSTRACT: ABSTRACT: Two facile synthetic approaches to the novel biologically interesting 1-thiocyclopropanecarboxylates starting from corresponding thiols were developed. Approach A involved five steps with the key steps being the SN 2 reactions of thiols and α-bromobutyrolactone and cyclopropane formation via t -BuOK-mediated intramolecular SN 2 cyclization. It had advantages such as inexpensive reagents and simplicity of operation but was associated with limitations such as relatively more reaction steps and incompatibility with thiols exhibiting acidic and alkaline functional groups. Approach B involved two steps with the key step being LDA-mediated cyclopropane formation at the α-position of carboxylate groups by use of 1, 3, 2-dioxathiolane-2, 2-dioxide. It showed advantages such as fewer reaction steps and simplicity of operation but was associated with limitations such as relatively expensive reagents and incompatibility with thiols exhibiting acidic functional groups. The two approaches are complementary in many respects, allowing for flexible choices according to specific requirements for the characteristics of synthetic methods.
- Is Part Of:
- Phosphorus, sulfur, and silicon and the related elements. Volume 192:Number 7(2017)
- Journal:
- Phosphorus, sulfur, and silicon and the related elements
- Issue:
- Volume 192:Number 7(2017)
- Issue Display:
- Volume 192, Issue 7 (2017)
- Year:
- 2017
- Volume:
- 192
- Issue:
- 7
- Issue Sort Value:
- 2017-0192-0007-0000
- Page Start:
- 799
- Page End:
- 811
- Publication Date:
- 2017-07-03
- Subjects:
- Synthetic approach -- cyclopropanecarboxylate -- 1-thiocyclopropanecarboxy-late -- cyclopropane formation
Sulfur compounds -- Periodicals
Organosulfur compounds -- Periodicals
Phosphorus compounds -- Periodicals
Organophosphorus compounds -- Periodicals
Silicon compounds -- Periodicals
Organosilicon compounds -- Periodicals
546 - Journal URLs:
- http://www.tandfonline.com/toc/gpss20/current ↗
http://www.tandfonline.com/ ↗ - DOI:
- 10.1080/10426507.2017.1286492 ↗
- Languages:
- English
- ISSNs:
- 1042-6507
- Deposit Type:
- Legaldeposit
- View Content:
- Available online (eLD content is only available in our Reading Rooms) ↗
- Physical Locations:
- British Library DSC - 6465.312000
British Library DSC - BLDSS-3PM
British Library HMNTS - ELD Digital store - Ingest File:
- 2836.xml