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The present work explored the primary factors governing regioselectivity of Wittig olefination in bicyclo[2.2.2]oct-5-en-2-ones having 5-aroyl or acyl substitutions. In absence of steric congestion less enolizable ketone kinetically favored the initial formation of the oxaphosphetane ring whereas, in presence of 1,3-interaction between phosphonium ylide and ketone substitutions could switch over the selectivity in other direction.