Synthesis of heterocyclic systems via 1,4-addition reactions of phenyl(bromodichloromethyl)mercury derived dichlorocarbene

Seyferth, Dietmar; Shih, Houng-Min

doi:10.1021/ja00806a053

Cited by 16 publications

(3 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Dichlorocarbene, generated from the thermolysis of phenyl(bromodichloromethyl)mercury (56), reacts with the ¡mine 53 to give ethyl 2-chloro-5-ethoxyoxazole-4-carboxylate (60) in 20-35% yield. 46 The oxazoline 59 arises from the formal 1.4-addition of dichlorocarbene to the N=C-C=0 system in 57. The C=C-C=0 system does not undergo similar 1.4-addition with dichlorocarbene.…”

Section: Cn (Ci)2c=cnhcormentioning

confidence: 99%

Chemistry of oxazoles

Turchi¹,

Dewar²

1975

Chem. Rev.

328

114

View full text Add to dashboard Cite

Section: Cn (Ci)2c=cnhcormentioning

confidence: 99%

Chemistry of oxazoles

Turchi¹,

Dewar²

1975

Chem. Rev.

328

114

View full text Add to dashboard Cite

“…3 Pyrolysis of those compounds of type 1 where R = CH3 and C2Hs proceeded in similar fashion to give products believed to have structure 2 on the basis of their spectroscopic properties (eq 2). The mixed halide (Et02C)2-(R02C)2NN=CX, o=cC Jcx + Rx rr 2a, 80% yield 2b, 75% yield 2c, 90% yield 2d, 94% yield (2) NN=CClBr gave a 10:1 mixture of 2a and 2b on pyrolysis.…”

Section: Resultsmentioning

confidence: 99%

Halomethyl-metal compounds. 71. Application of phenyl(trihalomethyl)mercurials in the preparation of heterocyclic compounds

Seyferth¹,

Shih²

1974

J. Org. Chem.

View full text Add to dashboard Cite

Pyrolysis of hydrazonodihalomethanes of type (RO&)zNN=CXt (R = Me, Et; X = C1, Br) resulted in formation, in high yield, of alkyl 5-halo-2-oxo-A4-1,3,4-oxadiazoline-3-carboxylates. A different mode of decomposition was observed when R = Ph. The reaction of PhHgCXzBr (X = C1 and Br) with azodibenzoyl gave the respective benzoyl halide and 2-halo-5-phenyl-1,3,4-oxadiazole in a reaction that may have involved initial l,$-addition of CX2 to the N=NC=O system. Reaction of PhHgCClzBr with R02CN=C(C02Et)2 (R = Me or Et) resulted in formation of ClCOzR and the 2-chloro-4-carboethoxy-5-ethoxy-1,3-oxazole 16. The possible mechanisms of these reactions are discussed.In the previous paper of this series,l we reported concerning the reaction of phenyl(trihalomethy1)mercurials with azodicarboxylate esters (eq 1). We now report exten-PhHgCX, -I-R02CN=NCOsR --+ BO"PhHgX + (RO$)zNNeCX, (1) 1 X = C1, Br; R = Me, Et, Me&, PhCH,, Ph sions of this research which have led to new preparative routes to heterocyclic compounds.

show abstract

“…** 5 The involvement of nitrenes is assumed in this instance by analogy with other reactions, * fl~1 * 3 is regarded as one of the possible variants, and as a rule has not been reliably demonstrated (cf. for example, Butler 38 and Dyall, 39 Spagnolo et al, " 7 Spagnolo et al, 1 * 8 etc. ); at the same time even formally very similar compounds can have different mechanisms.…”

Section: >31mentioning

confidence: 99%