New thermal rearrangements of vinylogous ketoketenes and related intermediates

被引:2
作者
Cartwright, GA [1 ]
Gould, RO [1 ]
McNab, H [1 ]
机构
[1] UNIV EDINBURGH,DEPT CHEM,EDINBURGH EH9 3JJ,MIDLOTHIAN,SCOTLAND
关键词
D O I
10.1039/a702395b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2-Oxopyran-5-carbaldehydes (e,g, 3) containing a trapping group in the 5-position rearrange thermally by a sequence involving electrocyclic ring opening, E/Z isomerisation and ring closure; a similar strategy has enabled the first cases of thermal interconversion of pyran-2-ones and 2-pyridones, and of automerisation of 2-pyridones to be identified.
引用
收藏
页码:1293 / 1294
页数:2
相关论文
共 12 条
[1]  
[Anonymous], 1986, SHELX86 PROGRAM CRYS
[2]   PYROLYSIS OF 2-PYRONE, COUMARIN, AND 2-PYRIDONE [J].
BRENT, DA ;
HRIBAR, JD ;
JONGH, DCD .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (01) :135-&
[3]   Studies on lactones related to the cardiac aglycones. VI. The action of diazomethane on certain derivatives of alpha-pyrone [J].
Fried, J ;
Elderfield, RC .
JOURNAL OF ORGANIC CHEMISTRY, 1941, 6 (04) :577-583
[4]  
GOULD RO, 1985, CALC PROGRAM MOL GEO
[5]  
HICKSON CL, 1989, J CHEM RES-S, P176
[6]   2-PYRONECARBOXALDEHYDES [J].
KUREK, JT ;
VOGEL, G .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1968, 5 (02) :275-&
[7]   REARRANGEMENTS OF 2-PYRONES AND PYRAN-2-THIONES INVOLVING 1,5-SIGMATROPIC HYDROGEN SHIFTS [J].
PIRKLE, WH ;
TURNER, WV .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (11) :1617-1620
[8]   NMR SPECTRA OF 2-PYRONE AND 2-PYRONE DERIVATIVES [J].
PIRKLE, WH ;
DINES, M .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1969, 6 (01) :1-&
[9]  
SHELDRICK GM, 1976, SHELX PROGRAM CRYSTA
[10]  
*SIEM AN XRAY INST, 1992, SHELXTL PC VERS 4 3