메뉴 건너뛰기




Volumn 34, Issue 22, 1995, Pages 2524-2528

Synthesis of Novel Tetrathiafulvalene‐Based [3]Pseudocatenanes by Self‐Assembly; Prevention of trans/cis Isomerization

Author keywords

catenanes; crown ethers; self assembly; tetrathiafulvalenes

Indexed keywords


EID: 33750542705     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.199525241     Document Type: Article
Times cited : (58)

References (51)
  • 20
    • 0028963065 scopus 로고
    • For a review on the chemistry of 1,3‐dithiole‐2‐thione‐4,5‐dithiolate, see:, Synthesis
    • (1995) , pp. 215
    • Svenstrup, N.1    Becher, J.2
  • 40
    • 84985540843 scopus 로고    scopus 로고
    • TTF‐containing macrocyclic compounds have been prepared in most cases using a coupling reaction with trialkyl phosphites from the corresponding thiones (see ref.[6]). There are only few reports to date describing the synthesis of TTF‐derived macrocyclic systems starting directly from TTF‐containing precursors (see ref.[8]).
  • 42
    • 84985562914 scopus 로고    scopus 로고
    • The isomers could not be separated because they slowly interconverted in solution in the presence of trace amounts of acid; this was detected by thin layer chromatography (TLC). The first step (yielding 3 and 6) did not afford 2,3‐deprotected products (TLC indicated that no other important products formed except insoluble linear oligomers), although tetrathiafulvalene‐2,3,6,7‐tetrathiolate was produced quantitatively by treatment with eight equivalents of cesium hydroxide (see ref.[12]).
  • 44
    • 84985534395 scopus 로고    scopus 로고
    • All spectra were recorded with a Kratos MS50TC instrument operating at 4.7kV accelerating voltage and fitted with an electrospray ion source.
  • 46
    • 84985540886 scopus 로고    scopus 로고
    • 13C, DQ‐COSY, and NOESY spectra were recorded using standard pulse sequences. All chemical shifts are referenced to TMS.
  • 47
    • 37049083209 scopus 로고
    • Unsymmetric TTF compounds usually isomerize easily, catalyzed by trace amounts of acid. Two methods have been reported to be able to control the configurational interversion of TTF‐based macrocyclic systems. The first utilizes the difference in ring strain between the trans and cis configurations, see ref.[5] and also, J. Chem. Soc. Chem. Commun.
    • (1991) , pp. 843
    • Bertho‐Thoraval, F.1    Robert, A.2    Souizi, A.3    Boubekeur, K.4    Batail, P.5
  • 51
    • 84985509027 scopus 로고    scopus 로고
    • We have not yet studied the possibility of photochemical isomerization of these catenanes.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.