Abstract
This literature review focuses on the thermal rearrangement of O-aryl thiocarbamates to yield the corresponding S-aryl thiocarbamates: the Newman-Kwart rearrangement. The purpose of the review is to highlight the utility of the rearrangement which provides a key step in an efficient route to convert phenols into thiophenols. The scope of the Newman-Kwart rearrangement is illustrated by way of numerous examples of its application to the preparation of Ar-S species ranging from large-scale industrial processes through to the synthesis of complex organic molecules such as ligands and supramolecular structures. The review contains 238 references and covers just over 40 years of the literature, from the first reports of the rearrangement by Edwards and Pianka in 1965 up to mid-2007.
Original language | English |
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Pages (from-to) | 661-689 |
Number of pages | 29 |
Journal | Synthesis: Journal of Synthetic Organic Chemistry |
Issue number | 5 |
DOIs | |
Publication status | Published - 3 Mar 2008 |
Keywords / Materials (for Non-textual outputs)
- Newman-Kwart
- aryl thiocarbamates
- aryl thiols
- thermal rearrangement
- mechanism
- NONSTEROIDAL ANTIINFLAMMATORY AGENTS
- POTENTIAL PHOTOBIOLOGICAL ACTIVITY
- AXIALLY CHIRAL P,S-HETERODONOR
- ALDOSE REDUCTASE INHIBITORS
- SULFUR-CONTAINING POLYMERS
- THIA-FRIES REARRANGEMENT
- STERIC RATE ENHANCEMENT
- ASYMMETRIC CATALYSIS
- CONJUGATE ADDITION
- ACID-DERIVATIVES