As would be anticipated a-diaeosulphonea 1,2,3 , a new class of compounds recently prepared in our laboratory, are potential sulphonylcsrbene forming agents. The most conclusive way of trapping a carbene is by reaction with an olefin to produce a cyclopropane derivative. Indeed, when p-methowphenyls
Chemistry of α-diazosulphones: Part I. Preliminary Communication
✍ Scribed by J. Strating; A. M. van Leusen
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 121 KB
- Volume
- 81
- Category
- Article
- ISSN
- 0165-0513
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✦ Synopsis
Abstract
The preparation of the first representative of the hitherto unknown α‐diazosulphones, RSO~2~CHN~2~, is described.
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Aryl-and alkyl-sulphonyldiazomethenee (I) have been prepared by alkaline decomposition of substituted nitrosourethanes (1).
## Abstract Using the readily accessible chiral auxiliaries **1**–**3** the sulfonamide‐shielded __O__‐silylated esters **5** underwent π‐face‐selective α‐acetoxylation on successive treatment with Pb(OAc)~4~ and NEt~3~ HF to give after recrystallization α‐acetoxy ester **6** in 55–67% yields and i
## Abstract Secondary and tertiary carboxylic methyl or ethyl esters (**2a‐c**) were converted with trimethylslylmethyllithium (**3a‐c**) in high yields. Under identical reaction conditions the primary esters **2d,e** gave **3d, e** in lower yields. Since the trimethylsilyl (TMS) group α to a keton