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Volumn 71, Issue 3, 2006, Pages 1002-1008

Further characterization of mitsunobu-type intermediates in the reaction of dialkyl azodicarboxylates with P(III) compounds

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; ESTERIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; PHOSPHORUS COMPOUNDS; X RAY DIFFRACTION ANALYSIS;

EID: 32144451667     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051997x     Document Type: Article
Times cited : (30)

References (76)
  • 1
    • 32144461373 scopus 로고
    • review
    • Selected references: (a) Mitsunobu, O. Synthesis 1981, 1 (review).
    • (1981) Synthesis , vol.1
    • Mitsunobu, O.1
  • 2
    • 0000414496 scopus 로고
    • review
    • (b) Hughes, D. L. Org. React. 1992, 42, 335 (review).
    • (1992) Org. React. , vol.42 , pp. 335
    • Hughes, D.L.1
  • 18
    • 4544227240 scopus 로고    scopus 로고
    • Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; VCH: Wienheim, Chapter 10.3, (review)
    • (r) Dembinski, R. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; VCH: Wienheim, 2004; Chapter 10.3, pp 190-202 (review).
    • (2004) Handbook of Fluorous Chemistry , pp. 190-202
    • Dembinski, R.1
  • 19
  • 41
  • 55
    • 0001008110 scopus 로고    scopus 로고
    • Compounds of type 9 are interesting examples of pentacoordinate phosphoranes with "reversed apicophilicity". This aspect has been discussed by us as well others elsewhere. See ref 9 and (a) Timosheva, N. V.; Chandrasekaran, A.; Prakasha, T. K.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1996, 35, 6552.
    • (1996) Inorg. Chem. , vol.35 , pp. 6552
    • Timosheva, N.V.1    Chandrasekaran, A.2    Prakasha, T.K.3    Day, R.O.4    Holmes, R.R.5
  • 58
    • 0012031855 scopus 로고
    • An interesting point related to the two structures, as regards phosphorus chemistry, is that the P-NH-t-Bu group and the P-OR (Ar) groups are cis in 10, whereas they are trans in 11. This has some relevance to cyclodiphosphazane chemistry but is not elaborated here. For cis-trans isomerization in cyclodiphosph(III)azanes, see: (a) Reddy, V. S.; Krishnamurthy, S. S.; Nethaji, M. J. Organomet. Chem. 1992, 438, 99.
    • (1992) J. Organomet. Chem. , vol.438 , pp. 99
    • Reddy, V.S.1    Krishnamurthy, S.S.2    Nethaji, M.3
  • 60
    • 32144436111 scopus 로고    scopus 로고
    • note
    • This statement is corroborated by the observation of additional partners for hydrogen bonding in the structures of following compounds (phenol in B and water in C) (Bhuvan Kumar, N. N.; Manab Chakravarty; Kumara Swamy K. C., submitted for publication).
  • 63
    • 32144450449 scopus 로고    scopus 로고
    • note
    • 4OH)] (A), probably by partial decomposition. At room temperature, there appeared to be extensive deformation of the crystallinity. The data quality was not good, but by comparison of the bond parameters to structure of 18, it does support the formulation 17 for these products. An ORTEP picture (Figure S5) with bond parameters around phosphorus is available as Supporting Information.
  • 67
    • 32144449562 scopus 로고    scopus 로고
    • note
    • 3P-DMAD system in another paper quoted in ref 13 above.
  • 73
    • 0004283942 scopus 로고    scopus 로고
    • Siemens Area Detector Absorption Correction; University of Göttingen: Germany
    • Programs used: (a) Sheldrick, G. M. SADABS, Siemens Area Detector Absorption Correction; University of Göttingen: Germany, 1996
    • (1996) SADABS
    • Sheldrick, G.M.1
  • 74
    • 0004150157 scopus 로고    scopus 로고
    • A package for structure solution and refinement; University of Göttingen: Germany
    • (b) Sheldrick, G. M. SHELX-97, A package for structure solution and refinement; University of Göttingen: Germany, 1997.
    • (1997) SHELX-97
    • Sheldrick, G.M.1
  • 76
    • 32144441840 scopus 로고    scopus 로고
    • note
    • This compound is available from Aldrich (cat. no. 15, 595-0).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.