By Saul (editor) Patai
Chapter thirteen Carbonylation of main?group organometallic compounds (pages 799–962): Norma Nudelman
Chapter 14 Rearrangements regarding allenes (pages 963–1060): Samuel Braverman
Chapter 15 1,1?Diarylalkenes (pages 1061–1130): William S. Murphy
Chapter sixteen Fulvenes (pages 1131–1268): M. Neuenschwander
Chapter 17 The thiocarbonyl staff (pages 1269–1367): Ernst Schaumann
Chapter 18 Cycloadditions of enones (pages 1369–1565): Janine Cossy, Pierre?Alain Carrupt and Pierre Vogel
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Extra info for Double-Bonded Functional Groups: Volume 2 Part 2 (1989)
The hydrate 59, a white, crystalline solid, initially formed, can be converted thermally to 60, a yellow liquid which is very hygroscopic, exposure to moisture sufficing to convert it to 59 again n-C4HgLi iEt02CCH2CH2C02Et co n-C -1lO0C H CCCH2CH2C02Et '110 II0 (44) 63 '10 Li+ t-CqHgLi co -llooc + MeOC-COMe11 11 0 0 0- t-C I I OMe H C-C-CO2Me 0 aq. work-up OMe OH I II 0 I I t-C H C-C-C02Me t-CqH gC-CCOfle ' 1 10 I OH OSiMe3 t - C4 HSC-C-C-OMe II 0II 0II 0 (60) SCHEME 5 Lactones are cyclic esters and these also may be acylated via 'in situ' RLi/CO reactions.
Mixtures of cyclic and acyclic products were obtained with six- and seven-membered ring lactones (equations 47 and 48). 64% 16% (47) 57 parts 43parts (48) In the case of all substrates-ketones, aldehydes and esters-Seyferth's groups9 achieved marked improvement by using a 1:1 RLi/organic electrophile stoichiometry, and when the temperature was lowered to - 135 "C. The yields of the desired acylated products increased significantly and a concomitant decrease in the amount of undesirable by-products was realized.
And for the corresponding organometallic species66-68. Such geometry optimization led to the discovery of rather remarkable non-tetrahedral bridged structures66 and also revealed that the energies of standard geometry forms63 were often not representative6’. A commonly cited work on the calculated thermodynamic stability of carbonyl anions is S ~ h l e y e r ’ smolecular ~~ orbital examination. Schleyer used the semiempirical MND07’ method for the study of large carbanions and MNDO and ‘ab initio’ (the Gaussian 76 series of programs were initially employed)71for the smaller anions.