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Tetrahedron Letters

Volumn 23, Issue 46, 1982, Pages 4765-4768

Substituent effects on 2-aza-5-hexynyl radical cyclization regiochemistry

(3) Choi, Joong Kwon a Hart, David J a Tsai, Yeun Min a

a OHIO STATE UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000432088 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)85708-1 Document Type: Article

Times cited : (58)

References (19)

1
- 33845553580
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 1430
- Hart¹ Tsai²

2
- 84918352812
- α-Thiophenoxylactams 3,8 (mp 42–43°C), and 15 were prepared from the corresponding imides via the route described in overall yields of 76%, 83%, and 36%, respectively.

3
- 84918352811
- A 0.25M solution of tri-n-butyltin hydride (1.3 equivalents) in benzene containing 0.04 equivalents of AIBN was added to a 0.058M solution of the thiophenoxylactam (1.0 equivalents) in benzene via syringe pump over a 19 h period.

4
- 37049091461
- Some guidelines for radical reactions
- For the definition of endo and exo cyclization see
- (1980) Journal of the Chemical Society, Chemical Communications , pp. 482
- Beckwith¹ Easton² Serelis³

5
- 84918352810
- Enamide i was also produced during the catalytic hydrogenation. The ratio of 6:7:i was 1.8:1:1.2 by GC.

6
- 84918352809
- 13C-NMR spectra consistent with the assigned structures.

7
- 0011170165
- For references see, P. Demayo, Academic Press, New York
- (1980) Rearrangements in Ground and Excited States , vol.1 , pp. 202-203
- Beckwith¹ Ingold²

8
- 84918352808
- For some indolizidine alkaloids with substituent patterns related to 5 see Johns, S.R.; Lamberton, J. A. in “The Alkaloids”, Manske, R. H. F., Ed.; Academic Press, New York, Vol. 14.

9
- 0000382297
- New synthesis of .beta.-agarofuran and of dihydroagarofuran
- A terminal trimethylsilyl heptynyl radical cyclization has been reported:
- (1979) The Journal of Organic Chemistry , vol.44 , pp. 546
- Büchi¹ Wüest²

10
- 84918352807
- 1H-NMR spectrum of a purified mixture of products. Pure samples of 9–11 were obtained by a combination of GC and LC techniques. The ratio of 10:11 was approximately 1.7 although the identity of the major vinylsilane remains unknown.

11
- 0003085736
- Olefins from vinylsilanes by hydrolysis in the presence of p-toluenesulfinic acid
- Both 10 and 11 independently gave 12 upon protodesilylation.
- (1977) Tetrahedron Letters , pp. 4305
- Buchi¹ Wüest²

12
- 84918352806
- The ratio of 13:14, separable by GC, was 3.5.

13
- 84918352805
- Pyrrolizidinone 12 was prepared in a 50% overall yield from 8 on a 10 mmol scale.

14
- 84918352804
- 15a although this effect has not been observed for alkenyl radicals.

15
- 0009621053
- and references cited therein
- (1978) J Org. Chem. , vol.43 , pp. 1285
- Wilt¹ Aznavoorian²

16
- 0019768505
- For several applications of this radical-stabilizing effect to synthetic problems see:
- (1981) J. Org. Chem. , vol.46 , pp. 4825
- Swenton¹ Anderson² Jackson³ Narsimhan⁴

17
- 37049107290
- Synthesis and chemistry of 2-trimethylsilylbenzocyclobutenones
- (1981) Journal of the Chemical Society, Chemical Communications , pp. 179
- Chenard¹ Slapak² Anderson³ Swenton⁴

18
- 84918352803
- Product ratios were obtained as described. The ratio of 17:18 was 2.2 although the identity of the major vinylsilane remains unknown.

19
- 84918352802
- 7) afford roughly equal mixtures of pyrrolizidinones and indolizidinones. In all cases, reduction of 2 is the major reaction pathway under the conditions outlined.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.