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Volumn 2, Issue 8, 1996, Pages 1014-1023

Photoreactions of phenyl-substituted N-(pent-4-enyl-1-oxy)pyridine-2(1H)- thiones

Author keywords

Alkoxy radicals; Cyclizations; Pyridinethiones radicals; Tetrahydrofurans

Indexed keywords

ALKOXY RADICALS; CYCLIZATIONS; PYRIDINETHIONES RADICALS; REARRANGEMENT REACTIONS; STEREO-SELECTIVE; TETRA-HYDROFURAN; TETRAHYDROFURANS; TRANSITION STATE;

EID: 0000217511     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020818     Document Type: Article
Times cited : (46)

References (58)
  • 1
    • 84890849054 scopus 로고
    • (Eds.: L. B. Wingard, Jr., T. M. Brody, J. Larner, A. Schwartz), Wolfe Publishing, London
    • a) P. H. Doukas in Human Pharmacology (Eds.: L. B. Wingard, Jr., T. M. Brody, J. Larner, A. Schwartz), Wolfe Publishing, London, 1991, pp. 95-113;
    • (1991) Human Pharmacology , pp. 95-113
    • Doukas, P.H.1
  • 35
    • 84890838736 scopus 로고
    • Chem. Abstr. 1984, 100, 209113s;
    • (1984) Chem. Abstr. , vol.100
  • 38
    • 0000012312 scopus 로고
    • (Ed. J. D. Morrison), Academic Press, New York
    • b) P. A. Bartlett, in Asymmetric Synthesis, Vol. 3 (Ed. J. D. Morrison), Academic Press, New York, 1984, pp. 411-453.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 411-453
    • Bartlett, P.A.1
  • 40
    • 84890823837 scopus 로고    scopus 로고
    • note
    • o = 1.8 M 1.2 equiv) with AiBN as initiator yielded the product 14a in (96±1)% yield (cis:trans=89:11). In the same manner 14a (cis:trans = 30:70) was obtained from 2-iodomethyl-5- phenyltetrahydrofuran in quantitative yield (three individual runs). Each of the probes investigated showed no signals of the alcohol 4a in the gas chromatogram of the crude reaction mixture, thus ruling out a radical-induced ether cleavage 3a → 2a under the chosen reaction conditions.
  • 42
    • 84890825703 scopus 로고    scopus 로고
    • note
    • ref
  • 43
    • 84890853720 scopus 로고    scopus 로고
    • note
    • The driving force of the rearrangements 6a,h → 7a,h obviously is the formation of the heteroaromatic pyridine N-oxides 7a,h from the cross-conjugated cyclic olefins 6a,h.
  • 47
    • 33845375140 scopus 로고
    • The lowest energy geometry of the transition state of the 5-exo-trig reaction of 2a (Fig. 1) is taken from molecular modeling studies, which use restraints for the transition-state parameters (bond lengths and angles) of the reacting centers obtained from ab initio calculations (UHF/3-21G) on the addition of the methoxy radical to 1-propene
    • The lowest energy geometry of the transition state of the 5-exo-trig reaction of 2a (Fig. 1) is taken from molecular modeling studies, which use restraints for the transition-state parameters (bond lengths and angles) of the reacting centers obtained from ab initio calculations (UHF/3-21G) on the addition of the methoxy radical to 1-propene: K. N. Houk, M. N. Paddon-Row, D. C. Spellmeyer, N. G. Rondan, S. Nagase, J. Org. Chem. 1986, 51, 2874- 2879.
    • (1986) J. Org. Chem. , vol.51 , pp. 2874-2879
    • Houk, K.N.1    Paddon-Row, M.N.2    Spellmeyer, D.C.3    Rondan, N.G.4    Nagase, S.5
  • 48
    • 0842341771 scopus 로고
    • The geometry of the modeled transition structure was optimized using the implemented AM1/UHF wavefunction of the HyperChem® software package on a IBM-compatible Pentium machine. HyperChem® is available from Hypercube, 419 Phillip St. Waterloo, Ontario, Canada, N2L3X2. The distance between the proximal ortho hydrogen (b-H) and the pseudoequatorial hydrogen atom on C-2 in this picture is 2.43 Å
    • The geometry of the modeled transition structure was optimized using the implemented AM1/UHF wavefunction (M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909) of the HyperChem® software package on a IBM-compatible Pentium machine. HyperChem® is available from Hypercube, 419 Phillip St. Waterloo, Ontario, Canada, N2L3X2. The distance between the proximal ortho hydrogen (b-H) and the pseudoequatorial hydrogen atom on C-2 in this picture is 2.43 Å.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3902-3909
    • Dewar, M.J.S.1    Zoebisch, E.G.2    Healy, E.F.3    Stewart, J.J.P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.