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Volumn 37, Issue 14, 1996, Pages 2445-2448

Retro-ene type fragmentation of allylic dithiolcarbonates

Author keywords

[No Author keywords available]

Indexed keywords

SULFIDE;

EID: 0029945595     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00314-0     Document Type: Article
Times cited : (15)

References (15)
  • 2
    • 0016682362 scopus 로고
    • K. Harano and T. Taguchi, Chem. Pharm. Bull., 1972, 20, 2348, 2357: 1975, 23, 467.
    • (1975) Chem. Pharm. Bull. , vol.23 , pp. 467
  • 8
    • 85030197221 scopus 로고    scopus 로고
    • note
    • Heating of a 1:1 inclusion compound (ß-CyD-2a) at 120 °C for 6h, followed by treatment with aq. DMSO and extraction with benzene gave pure E-(3-phenylallyl) methyl sulfide (E-3a) in 81 % yield. The S-acetylmethyl derivative smoothly extruded COS to give the corresponding sulfide in 90% yield. The methyl substituent on 2-position of the allylic moiety retarded the reaction rate.
  • 9
    • 85030187502 scopus 로고    scopus 로고
    • note
    • 2 (0.1 eq) is 13.5 kcal/mol. (formula presented)
  • 10
    • 0002228091 scopus 로고
    • J. J. P. Stewart, QCPE Bull., 1989, 9, 10: idem, J. Comp. Chem., 1989, 10, 209, 221.
    • (1989) QCPE Bull. , vol.9 , pp. 10
    • Stewart, J.J.P.1
  • 11
    • 84988129057 scopus 로고
    • J. J. P. Stewart, QCPE Bull., 1989, 9, 10: idem, J. Comp. Chem., 1989, 10, 209, 221.
    • (1989) J. Comp. Chem. , vol.10 , pp. 209
    • Stewart, J.J.P.1
  • 12
    • 85030193572 scopus 로고    scopus 로고
    • note
    • Steric effect may be operative. Inspection of the optimized structures indicates that the OC - SCHRCH= bond of the secondary ones is elongated as compared with the primary ones.
  • 15
    • 85030192426 scopus 로고    scopus 로고
    • note
    • The MO simulations on proton-coordinated reaction for 2A implied a different mechanism, i.e., [3,3]-sigmatropic rearrangement. The 6-31G* simulation predicts that fragmentation of COS does not occur and betaine-type intermediate is produced.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.