메뉴 건너뛰기
Tetrahedron Letters
Volumn 22, Issue 46, 1981, Pages 4651-4654
A cyclobutene bridgehead olefin approach to the germacranes
Author keywords

[No Author keywords available]
Indexed keywords

EID: 0013536835     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(01)83004-5     Document Type: Article
Times cited : (22)
References (18)
  • 4
    • 84987299272 scopus 로고
    • A Chemical Study ofBurley Tobacco Flavour (Nicotiana tabacum L.). III. Structure Determination and Synthesis of 5-(4-Methyl-2-furyl)-6-methylheptan-2-one (?Solanofuran?) and of 3,4,7-Trimethyl-1,6- dioxa-spiro[4.5]dec-3-en-2-one(?Spiroxabovolide?), Two New Flavour Components ofBurley Tobacco
    • For example, 1,4-oxidation of a similar diene has been reported via reaction with singlet oxygen
    • (1973) Helvetica Chimica Acta , vol.56 , pp. 265
    • Demole1    Demole2    Berthet3
  • 9
    • 84919016489 scopus 로고    scopus 로고
    • No appreciable rearrangement was observed in the absence of the crown ether.
  • 10
    • 0000305490 scopus 로고
    • For a recent review on aspects of bridgehead olefin chemistry, see
    • (1980) Tetrahedron , vol.36 , pp. 1683
    • Shea1
  • 11
    • 84919016487 scopus 로고    scopus 로고
    • The details of this transformation will be reported shortly.
  • 12
    • 84919016486 scopus 로고    scopus 로고
    • −1; GC-MS: m/e = 164 (M+).
  • 13
    • 0019133097 scopus 로고
    • 3 of hydrogen on the cyclobutene. For a similar structural proof on an isomeric system, see
    • (1980) Tetrahedron Lett. , pp. 4547
    • Kahn1
  • 15
    • 84919016485 scopus 로고    scopus 로고
    • 3, 270 MHz): 6.11 δ (d,J = 16.1 Hz, 1H), 5.38 δ (dt, Jd = 16.1 Hz, Jt = 7.4 Hz, 1H), 4.90 δ (bs, 1H), 4.88 δ (bs, 1H); FT-IR (neat): 3075, 1702, 1649, 982, 889 cm-1; UV (hexane): λmax = 236 nm.; GC-MS: m/e = 164 (M+).
  • 16
    • 84919016484 scopus 로고    scopus 로고
    • When either pure cis (7) or pure trans (8) isomer was resubjected to the reaction conditions (180°, 12 hours) only a small degree of interconversion (<10%) took place, indicating the 5:1 cis:trans thermolysis ratio reflects a kinetic preference in the ring opening.
  • 17
    • 0004214006 scopus 로고
    • For a discussion of photoisomerization of dienes, see, McGraw Hill Book Co, N.Y, Ch. 2., section 2.1
    • (1966) Organic Photochemistry
    • Kan1
  • 18
    • 84919016483 scopus 로고    scopus 로고
    • Under these conditions, no electrocyclic ring closure of the dienes back to the cyclobutene 6 was detected.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.