SCOPUS 정보 검색 플랫폼

Volumn 16, Issue 19-20, 1975, Pages 1549-1552

Cycloaddition of N-phenyltriazolinedione to octamethylsemibullvalene and relative ease of nitrogen extrusion from the derived azo adducts

Author keywords

[No Author keywords available]

Indexed keywords

EID: 49549145042 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)72194-0 Document Type: Article

Times cited : (15)

References (20)

2
- 33847788020
- Prepared from the urazole by the method of
- (1966) J. Org. Chem. , vol.31 , pp. 3444
- Stickler¹ Pirkle²

3
- 84981766788
- Octamethylsemibullvalene
- (1968) Angewandte Chemie International Edition in English , vol.7 , pp. 537
- Criegee¹ Askani²

5
- 84981778017
- The Conservation of Orbital Symmetrya
- (1969) Angewandte Chemie International Edition in English , vol.8 , pp. 781
- Woodward¹ Hoffmann²

6
- 0002904928
- Possible examples of such a cycloaddition have been reported by
- (1971) Tetrahedron Lett. , pp. 935
- Baldwin¹ Pinschmidt²

8
- 84918281626
- A satisfactory elemental analysis was obtained for this compound.

9
- 84918281625
- The nmr spectrum of 1 proved temperature dependent. At low temperatures the resonance at high field for the bridgehead methyls was considerably broadened, although even at −100° it was not resolved into two separate peaks. This may indicate flipping of the urazole ring with a low barrier to planarity in the hydrazide nitrogens.

10
- 84918281624
- Even at lower temperatures the reaction between OMSB and PTAD is so fast that we were unable to study the effect of solvent polarity on the rate.

11
- 84918281623
- 3 solution of 1 or by stirring such a solution over silica gel. Use of Quanta Gram PQ 5F preparative plates was found to allow the separation of 1 from 2 without isomerization.

12
- 20644469963
- Allyl radicals from 3,3′-azo-1-propene
- (1970) Canadian Journal of Chemistry , vol.48 , pp. 2745
- Al-Sader¹ Crawford²

13
- 84918281622
- Only one bond is thought to cleave in the transition state for decomposition of 3,3′-azo-1-propene [R. J. Crawford and K. Takagi, J. Amer. Chem. Soc., 94, 7406 (1972)] and the correspondence between this compound and 4 in rate of nitrogen loss suggests a similar transition state for decomposition of 4. In contrast, rate studies [M. Schneider and G. Mossinger, Tetrahedron Lett., 3081 (1974) and R. J. Crawford and M. Ohno, Can. J. Chem., 52, 3134 (1974)] show that in 3,5-divinylpyrazolines, other than 4, both vinyl groups stabilize the transition state, implying concerted nitrogen extrusion.

14
- 0000961994
- have independently prepared this azo ester and put it to a similar use.
- (1973) J. Amer. Chem. Soc. , vol.95 , pp. 7325
- Semmelhack¹ Foos² Katz³

15
- 84918281621
- R. Aksani has informed us (private comnunication) that he has observed similar behavior in 3, which he prepared by a route different than ours.

16
- 0012610569
- See, for instance, and references therein
- (1969) J. Amer. Chem. Soc. , vol.91 , pp. 5668
- Rieber¹ Alberts² Lipsky³ Lemal⁴

17
- 0009486259
- Photochemical and thermal 1,2- and 1,4-cycloaddition reactions of azodicarbonyl compounds with monoolefins
- (1970) The Journal of Organic Chemistry , vol.35 , pp. 1155
- van Gustorf¹ White² Kim³ Hess⁴ Leitish⁵

18
- 0039820105
- (1971) J. Org. Chem. , vol.36 , pp. 2838
- Turner¹ Guilbault² Butler³

19
- 84981915765
- 1,4-Cycloaddition of Azodicarboxylic Phenylimide [4-Phenyl-1,2,4-triazoline-3,5-dione] to Cyclooctatetraene and Its Halogen Derivatives
- (1972) Angewandte Chemie International Edition in English , vol.11 , pp. 715
- Huisgen¹ Konz² Schnegg³

20
- 84995195204
- Attempts to Synthetize Tetramethylyclobutadiene
- (1962) Angewandte Chemie International Edition in English , vol.1 , pp. 519
- Criegee¹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.