By R. B. Woodward
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Extra resources for The conservation of orbital symmetry
W . Theobald, J. Amer. chem. 82, 1428 (1960); D. J. Cram, C . S. Montgomery, and G . R . Knox,ibid. 88, 515 (1966); D . J. Cram, C. K. Dalton, and G . R. Knox, ibid. 85, 1088 (1963); D . T. -P. Boettcher, ibid. 85, 3436 (1963). 1971 T. Mukai, T . Tezuka, and Y . Akasaki, J. Amer. chem. Soc. 88, 5025 (1966).  A . S. Kende and J . E. Lancaster, J. Amer. chem. SOC. 89. 5283 (1967). 815 Cycloadditions involving ionic components are as yet not common. Ionic [4+2] cycloadditions may be realized in a number of different ways [(202)-(204)].
LeMahieu, and R . B. Mitra, J. Amer. chem. 86, 5570 (1964); P. E. Eaton and K. Lin, ibid. 86, 2087 (1964); A . Cox, P. de Mayo, and R . W . Yip,ibid. 88,1043 (1966); R . Robson, P. W . Grubb, and J . A . Barltrop, J. chem. SOC. 1964,2153. [61a] H . Yamazaki and R . J . CvetanoviC, J. Amer. chem. SOC. 91, 520 (1969). 81 1 H M c- @ (15la) Further, a pretty example (151b) of the photochemical [D2s+,2s] reaction has been discovered [61bJ. It is quite possible that the reversal of the simplest [2+2] cycloaddition, the pyrolysis of cyclobutane, is not a concerted process.
F. M . O f h , Angew. Chem. 80,633 (1968); Angew. Chem. internat. Edit. 7, 646 (1968); Rec. Trav. chim. Pays-Bas 87,1185 (1968). Angew. Chem. internat. Edit. j Yo). 8 (1969) / No. I 1 Further insight into the basic nature of symmetry-determined bonding relationships can be gained by amplifying our discussion of prismane in a number of ways. First, let us note that, in a formal sense, the transformation of prismane into benzene might be regarded as a -[x2s+x2a+x2a] cycloreversion reaction [(300) +(301)].
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