An efficient synthesis of isothiazolidines via sulfonium ylides formed by the reaction of thietanes and nitrene

Tetrahedron Letters

Volumn 47, Issue 7, 2006, Pages 1109-1111

  Nair, Vijay ^a   Nair, Smitha M ^a   Devipriya, S ^a   Sethumadhavan, D ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

Isothiazolidine; Nitrene; Sulfonium ylide; Thietane

Indexed keywords

2 (4 CHLOROPHENYL)THIETANE; BENZENE; BENZENE DERIVATIVE; IMINE; ISOTHIAZOLE DERIVATIVE; ISOTHIAZOLIDINE; N (4 TOLYLSULFONYL) IMINO]PHENYLIODINANE; NITRENE; SULFONIUM DERIVATIVE; SULFONIUM YLIDE; THIETANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 30544447733     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.024     Document Type: Article

References (17)

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11. The diastereomeric mixture of thietanes used in our investigations was obtained from the corresponding 1,3-dibromide and sodium sulfide nonahydrate. The ratio of diastereomers in the case of 4d has been determined by HPLC analysis. 1,3-Dibromides in turn were prepared following the literature procedure. D.J.H. Smith, and M. Lancaster Synthesis 1982 582 583
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13. 2 under the same reaction conditions. However, the yield of 3a remained unchanged and toluenesulfonamide resulting from hydrolysis of the iodonium ylide was obtained.
14. The yields are reported on the basis of the nitrene precursor used.
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16. +]: 444.0103. Found: 443.9886.
17. HPLC analysis of a solution of thietane 4d in methanol before and after the reaction was carried out. The cis:trans ratios of 4d before and after the reaction were 1.9:1 and 0.5:1, respectively. Thus it was clear that only the cis isomer reacts. Experiments with varying amounts of PhINTs for a fixed amount of 4d revealed that the yield is invariable. When the reaction time and temperature were varied, poor yields of the product 5d resulted. We assume that there is an inherent kinetic selectivity for the cis isomer over the trans isomer.