Silanethione 2a and silaneselenone 2b—stabilized by intramolecular Si ← N coordination— are obtained as shown below. The X-ray structure analysis of 2a, 1-naphthyl instead of phenyl, reveals strong zwitterionic character, which might explain the unexpectedly low reactivity toward nucleophiles and electrophiles (a, X = S; b, X = Se).
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Arya et al. (1989) studied this question.