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Volumn , Issue 11, 1999, Pages 1944-1950

Ring-opening reactions of cyclopropanes. Part 6. A facile synthesis of dialkyl sulfenylbutanedioates

Author keywords

Cyclopropanes; Electrophilic bimolecular substitution; Selectivity; Sulfenyl chlorides; Sulfenylbutanedioates

Indexed keywords

CYCLOPROPANE; MALEIC ACID; SULFUR DERIVATIVE; THIOL;

EID: 0032732975     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3617     Document Type: Article
Times cited : (6)

References (49)
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    • Ref. 1 and preceding issues of the series
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    • 14 hydrolyze very easily; in particular, the former lead to the corresponding ethyl methyl butanedioates, which may be present occasionally in the reaction mixtures
    • 14 hydrolyze very easily; in particular, the former lead to the corresponding ethyl methyl butanedioates, which may be present occasionally in the reaction mixtures.
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    • 3, indicated the presence of MeCl. This could not be quantified owing to its volatility.
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    • 8 Control experiments showed that under above conditions 1c was recovered unchanged even after 10 h.
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    • note
    • 1H NMR spectral data with those of pairs 3f,h; in particular, syn-3e,g show signals due to chain methylenes in the δ range 1.7-2.2 and anti-3e,g in the δ range 1.5-1.7 as observed for syn-3f,h and anti-3f,h, respectively. In the reactions of 1b with 2b,c only one isomeric 2-sulfenyl-3-methylbutanedioate was obtained in moderate amount; thus, configuration of syn-3b and syn-3c was assigned on the basis of the general stereochemical course which leads to syn-3 as by far the main products.
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    • E2-type attack has been observed as reported in ref 7a
    • E2-type attack has been observed as reported in ref 7a.
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    • In the reactions of 1b,c with 2c a prevailing unidentified product was present which did not interfere in the chromatographic procedures as it is more polar than the reaction products
    • In the reactions of 1b,c with 2c a prevailing unidentified product was present which did not interfere in the chromatographic procedures as it is more polar than the reaction products.
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    • -1 for syn-6 and anti-6, respectively
    • -1 for syn-6 and anti-6, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.