منابع مشابه
S,C-sulfonium ylides from thiophenes: potential carbene precursors.
Photolysis of S,C-sulfonium ylides derived from thioanisol, thiophene, benzothiophene, or dibenzothiophene provides products deriving from dicarbomethoxycarbene. In methanol, no rearrangement of the carbene to the ketene derivative is observed. Formation of dibenzothiophene and benzothiophene is quantitative. For the thiophene-based ylide, insertion of the carbene into the alpha-CH bond of thio...
متن کاملThe asymmetric synthesis of terminal aziridines by methylene transfer from sulfonium ylides to imines.
A new ylide-based protocol for the asymmetric aziridination of imines via methylene transfer has been developed involving the use of a simple chiral sulfonium salt and an organic strong base. A systematic study identified triisopropylphenyl sulfonylimines as optimal substrates for the process. Unexpectedly, hindered C2-symmetric sulfonyl salts incorporating bulky ethers at C-2 and C-5--which ha...
متن کاملSulfur and selenium ylide bond enthalpies.
The bond dissociation enthalpies (BDEs) of sulfur and selenium ylides have been estimated by applying MP2/6-311++G(3df,2p)//MP2/6-31G(d,p), G3, and other computational methods. Computed sulfoxide bond enthalpies were compared to experimental results to ensure the reliability of the computational methods before extending to related compounds. The examined ylides include the following: sulfoxides...
متن کاملReactions of silyl-stabilised sulfur ylides with organoboranes: enantioselectivity, mechanism, and understanding.
The reaction of trimethylsilyl-substituted sulfonium ylides with organoboranes (Ph(3)B, Et(3)B) has been studied and although homologated products were obtained in good yield (after oxidation to the corresponding alcohols), the enantiomeric excesses were low with our camphor-based chiral sulfide (up to 40% ee, cf. corresponding phenyl-substituted sulfonium ylides gave >95% ee). Cross-over exper...
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ژورنال
عنوان ژورنال: Journal of Synthetic Organic Chemistry, Japan
سال: 1971
ISSN: 0037-9980,1883-6526
DOI: 10.5059/yukigoseikyokaishi.29.911