91-12-3Relevant articles and documents
LeVanda et al.
, p. 3181,3186 (1976)
Scherer
, p. 1550 (1963)
The reactions of diazo compounds with lactones. Part 1. Cyclopropanespiro-β-lactones from diketene: Synthesis and reactions
Murphy, Paul V.,O'Sullivan, Timothy J.,Geraghty, Niall W.A.
, p. 2109 - 2119 (2007/10/03)
The cyclopropanespiro-β-lactones 3, 4 and 12 can be prepared by the metal catalysed, or photochemically promoted decomposition reactions of diazocompounds in the presence of diketene. The thermal reactions of these compounds give a variety of products depending on the nature of the spirolactone; these include a furan 9a, 1,4-dicarbonyl compounds 18a-c and 19b, a pyranone 20b, furanones 21a, 21f and 22a and the enol 16. The boron trifluoride promoted reaction of a mixture of 3b and 4b gives a 13-ketoacid. Mechanisms are proposed for the formation of these products. The rearrangment of the cyclopropanespiro-β-lactones to furan-2(5H)-ones and furan-2-(3H)-ones 6-8, 21a, 21f, 22a and 24 is shown to be a general reaction that involves metal catalysis. A mechanism based on formation of a metallocycle by a novel insertion of the metal into the C-O bond of the β-lactone ring is proposed for this rearrangement. This accounts for the observed features of the reaction.
DIRECT IR-SPECTROSCOPIC OBSERVATION OF (1+2)-CYCLOADDITION OF CYCLOPENTADIENYLIDENE TO ETHYLENE IN ARGON MATRIX
Nefedov, Oleg M.,Zuev, Petr S.,Maltsev, Andrey K.,Tomilov, Yuri V.
, p. 763 - 764 (2007/10/02)
Cyclopentadienylidene was generated in argon matrix doped with 2percent C2H4 and the direct reaction of the carbene with C2H4 in matrix, when it was annealing from 12 to 40-45 K, was observed.