An efficient synthesis of some substituted vinylic chloroformates: reaction scope and limitations

Bowman, Mark P.; Senet, J.‐P. G.; Malfroot, Thierry; Olofson, R. A.

doi:10.1021/jo00311a015

Cited by 13 publications

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“…3.1. Synthesis of Diazo Esters l l a , b and 20a-c. Vinyl diuzoacetate (lla), and 2-methylcyclohex-I-enyl diazoacetate (llb) were synthesized from vinyl chloroformate (Fluku) and 2-methylcyclohex-I-enyl chloroformate [35], respectively, and a 3-fold excess of freshly distilled etheral diazomethane (from Diuzuld). The diazo esters were purified by CC immediately before use.…”

Section: Presence Of Meohmentioning

confidence: 99%

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Rhodium(II)‐Catalyzed Decomposition of β,γ‐Unsaturated Diazo Compounds

Motallebi

Müller

1993

Helvetica Chimica Acta

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The Rh"-catalyzed decomposition of p,y-unsaturated diazo ketones 1 in the presence of MeOH leads uia vinylogous Wolffrearrangement to y,d-unsaturated esters 6 (Schemes I and 2). A modest asymmetric induction is achieved when the reaction is carried out with chiral tetrakis(pyrrolidinecarboxylato)-or tetrakis(oxazo1idino-nato)dirhodiuni(II) complexes. Vinyl and phenyl diazoacetates 11 and 20, respectively, or I-diazo-3-phenylpropan-2-one (25), when subjected to the same reaction conditions, xact by OH insertion with MeOH (Schemes 3-5). In the absence of MeOH, phenyl diazoacetates 20 and 25 undergo intramolecular CH insertion to 22 and 26, respectively. Intramolecular CH insertion occurs with N-aryldiazoamides 23 even in the presence of MeOH (Scheme 5 ) .

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Section: Presence Of Meohmentioning

confidence: 99%

“…The chloroformate required for the synthesis of 2.6-dimethylphenyl diazoacrtare (20c) was prepared by reaction of 2,6-dimethylphenol with an excess (3.0 equiv.) of phosgene in toluene [35]. lla: Yield 72%.…”

Section: Presence Of Meohmentioning

confidence: 99%