Matches in SemOpenAlex for { <https://semopenalex.org/work/W2093804974> ?p ?o ?g. }
- W2093804974 endingPage "2642" @default.
- W2093804974 startingPage "2631" @default.
- W2093804974 abstract "The thermal reaction of trans-1-methyl-2,3-diphenylaziridine (trans-1a) with aromatic and cycloaliphatic thioketones 2 in boiling toluene yielded the corresponding cis-2,4-diphenyl-1,3-thiazolidines cis-4 via conrotatory ring opening of trans-1a and a concerted [2+3]-cycloaddition of the intermediate (E,E)-configured azomethine ylide 3a (Scheme 1). The analogous reaction of cis-1a with dimethyl acetylenedicarboxylate (5) gave dimethyl trans-2,5-dihydro-1-methyl-2,5-diphenylpyrrole-3,4-dicarboxylate (trans-6) in accord with orbital-symmetry-controlled reactions (Scheme 2). On the other hand, the reactions of cis-1a and trans-1a with dimethyl dicyanofumarate (7a), as well as that of cis-1a and dimethyl dicyanomaleate (7b), led to mixtures of the same two stereoisomeric dimethyl 3,4-dicyano-1-methyl-2,5-diphenylpyrrolidine-3,4-dicarboxylates 8a and 8b (Scheme 3). This result has to be explained via a stepwise reaction mechanism, in which the intermediate zwitterions 11a and 11b equilibrate (Scheme 6). In contrast, cis-1,2,3-triphenylaziridine (cis-1b) and 7a gave only one stereoisomeric pyrrolidine-3,4-dicarboxylate 10, with the configuration expected on the basis of orbital-symmetry control, i.e., via concerted reaction steps (Scheme 10). The configuration of 8a and 10, as well as that of a derivative of 8b, were established by X-ray crystallography." @default.
- W2093804974 created "2016-06-24" @default.
- W2093804974 creator A5015059473 @default.
- W2093804974 creator A5019107967 @default.
- W2093804974 creator A5022355782 @default.
- W2093804974 creator A5031907447 @default.
- W2093804974 creator A5042377073 @default.
- W2093804974 creator A5076233754 @default.
- W2093804974 date "2009-12-01" @default.
- W2093804974 modified "2023-10-14" @default.
- W2093804974 title "Thermal [2+3]-Cycloadditions of trans-1-Methyl-2,3-diphenylaziridine with CS and CC Dipolarophiles: An Unexpected Course with Dimethyl Dicyanofumarate" @default.
- W2093804974 cites W1490975605 @default.
- W2093804974 cites W1579232371 @default.
- W2093804974 cites W1964616561 @default.
- W2093804974 cites W1965805570 @default.
- W2093804974 cites W1969857981 @default.
- W2093804974 cites W1975081287 @default.
- W2093804974 cites W1977430873 @default.
- W2093804974 cites W1978060694 @default.
- W2093804974 cites W1981911740 @default.
- W2093804974 cites W1982745477 @default.
- W2093804974 cites W1993105124 @default.
- W2093804974 cites W1996212147 @default.
- W2093804974 cites W1998490900 @default.
- W2093804974 cites W2002427606 @default.
- W2093804974 cites W2014142761 @default.
- W2093804974 cites W2022249530 @default.
- W2093804974 cites W2027454585 @default.
- W2093804974 cites W2029408587 @default.
- W2093804974 cites W2031202519 @default.
- W2093804974 cites W2035552792 @default.
- W2093804974 cites W2037150136 @default.
- W2093804974 cites W2045446945 @default.
- W2093804974 cites W2049850818 @default.
- W2093804974 cites W2052665507 @default.
- W2093804974 cites W2054379681 @default.
- W2093804974 cites W2068152199 @default.
- W2093804974 cites W2087182945 @default.
- W2093804974 cites W2114312014 @default.
- W2093804974 cites W2119903796 @default.
- W2093804974 cites W2142152229 @default.
- W2093804974 cites W2145385152 @default.
- W2093804974 cites W2148066840 @default.
- W2093804974 cites W2166052839 @default.
- W2093804974 cites W2169992767 @default.
- W2093804974 cites W2326809638 @default.
- W2093804974 cites W2820209543 @default.
- W2093804974 cites W2950077814 @default.
- W2093804974 cites W2950283738 @default.
- W2093804974 cites W2951205944 @default.
- W2093804974 cites W2952172386 @default.
- W2093804974 cites W2952664136 @default.
- W2093804974 cites W4246624998 @default.
- W2093804974 doi "https://doi.org/10.1002/hlca.200900236" @default.
- W2093804974 hasPublicationYear "2009" @default.
- W2093804974 type Work @default.
- W2093804974 sameAs 2093804974 @default.
- W2093804974 citedByCount "12" @default.
- W2093804974 countsByYear W20938049742014 @default.
- W2093804974 countsByYear W20938049742015 @default.
- W2093804974 countsByYear W20938049742017 @default.
- W2093804974 countsByYear W20938049742018 @default.
- W2093804974 countsByYear W20938049742020 @default.
- W2093804974 countsByYear W20938049742021 @default.
- W2093804974 crossrefType "journal-article" @default.
- W2093804974 hasAuthorship W2093804974A5015059473 @default.
- W2093804974 hasAuthorship W2093804974A5019107967 @default.
- W2093804974 hasAuthorship W2093804974A5022355782 @default.
- W2093804974 hasAuthorship W2093804974A5031907447 @default.
- W2093804974 hasAuthorship W2093804974A5042377073 @default.
- W2093804974 hasAuthorship W2093804974A5076233754 @default.
- W2093804974 hasConcept C106159729 @default.
- W2093804974 hasConcept C111771559 @default.
- W2093804974 hasConcept C14158195 @default.
- W2093804974 hasConcept C147597530 @default.
- W2093804974 hasConcept C155647269 @default.
- W2093804974 hasConcept C157103358 @default.
- W2093804974 hasConcept C161790260 @default.
- W2093804974 hasConcept C162324750 @default.
- W2093804974 hasConcept C176788430 @default.
- W2093804974 hasConcept C178790620 @default.
- W2093804974 hasConcept C185592680 @default.
- W2093804974 hasConcept C24961977 @default.
- W2093804974 hasConcept C2775855009 @default.
- W2093804974 hasConcept C2777600838 @default.
- W2093804974 hasConcept C2778142098 @default.
- W2093804974 hasConcept C2779167645 @default.
- W2093804974 hasConcept C2779664164 @default.
- W2093804974 hasConcept C2780378348 @default.
- W2093804974 hasConcept C32909587 @default.
- W2093804974 hasConcept C71240020 @default.
- W2093804974 hasConceptScore W2093804974C106159729 @default.
- W2093804974 hasConceptScore W2093804974C111771559 @default.
- W2093804974 hasConceptScore W2093804974C14158195 @default.
- W2093804974 hasConceptScore W2093804974C147597530 @default.
- W2093804974 hasConceptScore W2093804974C155647269 @default.
- W2093804974 hasConceptScore W2093804974C157103358 @default.
- W2093804974 hasConceptScore W2093804974C161790260 @default.