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Tetrahedron Letters

Volumn 21, Issue 35, 1980, Pages 3389-3392

Conjugated addition of cyanotrimethylsilane to α,β-unsaturated ketones

(5) Utimoto, Kiitiro a Obayashi, Michio a Shishiyama, Yuho a Inoue, Masaharu a Nozaki, Hitosi a

a KYOTO UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001429355 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)78696-5 Document Type: Article

Times cited : (50)

References (18)

1
- 0001032785
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 4635
- Nagata¹ Yoshioka² Hirai³

2
- 0039830400
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 4644
- Nagata¹ Yoshioka² Murakami³

3
- 0011153288
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 4654
- Nagata¹ Yoshioka² Murakami³

4
- 0038570340
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 4672
- Nagata¹ Yoshioka² Terasawa³

5
- 0000146934
- (1977) Org. React. , vol.25 , pp. 255
- Nagata¹ Yoshioka²

6
- 27144444200
- Cyanosilylation of aldehydes and ketones. A convenient route to cyanohydrin derivatives
- (1973) Journal of the Chemical Society, Chemical Communications , pp. 55
- Evans¹ Truesdale² Carroll³

7
- 33847805877
- (1974) J. Org. Chem. , vol.39 , pp. 914
- Evans¹ Carroll² Truesdale³

8
- 0000812802
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 5822
- Evans¹ Hoffman² Truesdale³

9
- 85067874645
- Nucleophile Acylierung mit verkappten Acylanionen
- (1973) Synthesis , pp. 777
- Deuchert¹ Hertenstein² Hünig³

10
- 3342959019
- S-Cyanosilylenolethers: Preparation and Potential Intermediates in Synthesis
- Cyanated siloxyalkenes of type B have been prepared by the conjugated addition of diethylaluminium cyanide to enones followed by trapping of the resulting aluminium enolates with chlorotrimethylsilane
- (1978) Synthetic Communications , vol.8 , pp. 231
- Samson¹ Vandewalle²

11
- 84914344999
- 4) besides methylene protons (δ 1.1–2.5, m, 12H) and methyl protons of trimethylsilyl group (δ 0.21, s, 9H), angular methyl protons (δ 0.94, s, IIb; δ 1.18, s, IIa, the sum was equal to 3H), olefin proton (δ 4.50, broad s, IIb; δ 4.58, broad s, IIa, the total integration corresponded to 1H).

12
- 84914344998
- Thermodynamically controlled conjugated hydrocyanation with diethylaluminium cyanide gives a mixture of IIIa and IIIb in 87/13 ratio, reportedly (ref. 1c).

13
- 84914344997
- Kinetically controlled reaction with diethylaluminium cyanide provides a mixture of IIIa and IIIb in 36/64 ratio. The ratio changes to 29/71 upon treatment with hydrogen cyanide-triethylaluminium in place of diethylaluminium cyanide (ref. 1c).

14
- 84914344996
- 3, 20 MHz), shows 13 carbon atoms: δ ppm, 1.57, 22.03, 23.35, 28.07, 32.13, 33.77, 34.94, 36.11, 41.53, 68.72, 121.10, 121.56, 149.34.

15
- 84914344995
- The absence of the additional cyanotrimethylsilane in the isomerization of IV to II has yielded a complex mixture, although the role of the cyanosilane is not clear yet. Following assumptions explain the observed rearrangement.

16
- 84914344994
- GLC of the crude product showed one peak with small shoulder. The structure of the major product could be assigned as VIII′ based on the proton signal (HCCN, δ 3.1 ppm, ΣJ = 10 Hz) which corresponds to the quasi-equatorial proton.

17
- 84914344993
- TLC (Kieselgel 60, benzene) indicated the homogeneity of the product. The structure X was determined by nmr analysis: a multiplet (HCCN, δ 3.2 ppm, 1H) changed to a double doublet (J = 4, 6 Hz) by double irradiation at a doublet (CCHCHCN, δ 5.0 ppm, J = 5 Hz, 1H). These observations suggest the stereochemistry of the proton geminal to cyano group should be equatorial.

18
- 84914344992
- 13C nmr measurement as well as the Ministry of Education, Science and Culture, Japan, for Grant-in-Aid (303023, 403022).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.