The 4J(H-C-C-Me) coupling constant, previously established1-3 as a probe of bond order, was used to examine the bond orders in a series of ortho -bridged compounds: benzocyclopropene , 1,2- dihydrobenzocyclobutene , indan and tetralin . No evidence for sterically induced bond fixation (i.e. the Mills-Nixon4 effect) was found, but some evidence for electronic distortion In the corresponding benzylic ketones was observed. The experimental results are in accord with SCF/MO calculations.
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Collins et al. (1990) studied this question.
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