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Volumn 36, Issue 29, 1995, Pages 5199-5202

Thermal cycloaddition reactions of 3-bromo-1,5-azulenequinone and 3-bromo-1,7-azulenequinone with 1,3-diphenylbenzo[c]furan

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIPHENYLBENZO[C]FURAN; 3 BROMO 1,5 AZULENEQUINONE; 3 BROMO 1,7 AZULENEQUINONE; ISOBENZOFURAN DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; STEREOISOMERISM; STRUCTURE ANALYSIS; THERMODYNAMICS; X RAY DIFFRACTION;

EID: 85033822195 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/00404-0399(50)0974H- Document Type: Article

Times cited : (1)

References (12)

1
- 0001359967
- Quinones of azulene. 4. Synthesis and characterization of the parent 1,5- and 1,7-quinones
- (1989) Journal of the American Chemical Society , vol.106 , pp. 4857
- Scott¹ Adams²

2
- 84914006429
- The term, [m+n], denotes the mode of the cycloaddition between mπ component of AQ or BAQ and nπ component of the counterparts.

4
- 0342690818
- Preparation of Various Azulenequinone Derivatives by a Nucleophilic Substitution of 3-Bromoazulenequinone Synthones.
- (1995) Chemistry Letters , pp. 27
- Nozoe¹ Wakabayashi² Shindo³ Ishikawa⁴

6
- 84914006426
- to be published elsewhere, (submitted)
- (1995) Tetrahedron Lett.
- Takeshita¹ Yan² Kato³ Mori⁴ Nozoe⁵

7
- 84914006425
- 3. Although a 1:1-mixture of 1 (obtained after removal of 2 by decomposition) and DIBF upon heating afforded 3 and 4, respectively. This could not assure the same stereochemistry for 3 and 4, as a possible cycloreversion of 1 into the cycloaddends under the conditions. And, indeed this was the case.

8
- 84914006424
- 3:1: δ(H)=3.61 (1H, s), 6.69(1H, dm, J=2.6 Hz), 7.02(1H, ddd, J=11.7, 2.6, 1.5 Hz), 7.2–7.6(12H, m), 7.39(1H, dd, J=11.7, 6.7 Hz), 7.83(1H, dd, J=6.7, 1.5 Hz), and 7.95(2H, ddm, J=8.4, 1.5 Hz).3: δ(H)=1.80(1H, dd, J=6.2, 1.1 Hz), 4.29(1H, s), 5.15(1H, dd, J=8.8, 6.2 Hz), 6.30(1H, d, J=8.8 Hz), 6.41(1H, s), 6.57(1H, dm, J=7.0 Hz), 6.86(1H, dm, J=7.0 Hz), 7.11–7.23(2H, m), 7.29–7.37(8H, m), 7.40–7.57(12H, m), 7.84–7.88(2H, m), and 8.02(2H, dm, J=7.0 Hz). δ(C)=47.1, 68.9, 76.3, 87.1, 89.9, 93.5, 105.1, 109.1, 120.4, 120.5(2C), 121.7, 121.9, 122.6, 125.3(2C), 126.1(2C), 126.5(3C), 126.6, 127.4(2C), 127.9(2C), 128.1, 128.3(4C), 128.5(3C), 129.0(2C), 129.5, 129.8, 135.3, 135.4, 136.7, 136.8, 137.1, 142.6, 143.1, 145.5, 146.5, 146.8, 159.0, and 198.1.4: δ(H)=2.27(1H, d, J=6.2 Hz), [[Truncated]]

9
- 84914006423
- 3 (8), respectively. Data collection was performed with Cu Kα radiation on an Enraf-Nonius FR590 computer controlled equipment. Structures were solved by direct method (SIR88; M. C. Burla et al., J. Appl. Crystallogr., 1989, 22, 389) and differential Fourier syntheses. Totals of 6550 reflections for 3 and 4226 reflections for 8 having intensities greater than 3.0 times their [[Truncated]]

10
- 1542746915
- Thermal cycloaddition reaction of tropone to 1,1-diethoxyethene. Structure revision of Cantrell's Diels-Alder adduct.
- There are several examples of [8+2] cycloadducts involving the tropone carbonyl group; e.g.
- (1988) Bulletin of the Chemical Society of Japan , vol.61 , pp. 573
- Takeshita¹ Nakashima² Sugiyama³ Mori⁴

12
- 84914006422
- 2 It is certain that 8 is its 3-bromo derivative. However, neither spectrum of 3 nor 4 was similar to that of another adduct from 5-AQ and DIBF [δ=3.45(d, J=6.4 Hz, H-2), 3.07(d, J=6.4 Hz, H-3), 4.13(d, J=1.8, H-4), 3.83(dd, J=6.9, 1.8 Hz, H-6), 5.41(dd, J=10, 6.9 Hz, H-7), and 5.88(d, J=10 Hz, H-8)].

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.