Rearrangement and fragmentation reactions of blocked aromatic alcohols
✍ Scribed by Bhattacharya, Ajit K.; Miller, Bernard
- Book ID
- 126960127
- Publisher
- American Chemical Society
- Year
- 1983
- Tongue
- English
- Weight
- 791 KB
- Volume
- 105
- Category
- Article
- ISSN
- 0002-7863
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## Abstract α‐Methylthio‐propiophenone __anti__‐oxime __p__‐toluenesulfonate (tosylate) (**12b**) fragments quantitatively in 80% ethanol yielding benzonitrile and a methylidenesulfonium ion **15**. The __syn__‐isomer, however, undergoes a __Beckmann__ rearrangement. The fragmentation of α‐methylth
## Abstract In 70% aqueous dioxane thian‐3‐one __anti__‐oxime __p__‐toluenesulfonate (tosylate) (**8b**) undergoes concerted fragmentation to the methylidenesulfonium ion **14**, part of which recyclizes to 1,3‐thiazepin‐4‐one (**11**). With the __syn__‐isomer **8b** rearrangement to 1,4‐thiazepin‐