83962-13-4Relevant academic research and scientific papers
7-Thiatetracyclo2,4.03,5>heptane (Benzvalene Sulfide) - Synthesis and Reactions
Leininger, Hartmut,Kemmer, Petra,Beck, Karin,Christl, Manfred
, p. 3213 - 3223 (2007/10/02)
The reaction of benzvalene (1) with N-(chlorothio)succinimide gives a mixture of the 1:1 adducts 5 and 6, the treatment of which with lithium aluminium hydride transforms 5 into 7-thiatetracyclo2,4.03,5>heptane (4).Among the elctrophiles studied only acids attack the bicyclobutane portion of 4 and produce 3-thia-trans-tricyclo2,4>heptanes (9) functionalized in the exo-5-position.Peracids transfer an oxygen atom to the sulfur atom of 4 to give the episulfoxide 7.Bromine and chlorine transform 4, probably via the sulfenyl halide intermediates 10, into the bis(trans-3-halotricyclo2,6>hex-4-yl disulfides 11 and 12.Mixtures of the disulfides 15 and 16 and the sulfides 19 and 20 are obtained from 4 and thiophenol under the conditions of a radical reaction.Most likely the attack of a phenylthiyl radical at the sulfur atom of 4 initiates the complex reaction sequence.
