Carbonization acenaphthylene scheme

The reaction schemes of carbonization have also been investigated (11-15). The molecular structure of the carbonization intermediates can influence strongly the optical anisotropy of the resultant coke. The carbonization intermediates have been reported for the pyrolysis of acenaphthylene, which provides a rare example of atmospheric carbonization of a pure organic chemical (11). The carbonization scheme is illustrated in Figure 2. The intermediates II, III, and VI are proposed based on... 

Figure 2. Carbonization scheme for acenaphthylene Reproduced with permission from reference 12. Copyright 1979 IPC Business Press, Ltd.

Thermolysis of trithiane (69) or carbonate (70) at reduced pressure yields methylene-thiirane which is stable in cold, dilute solution (Scheme 152) (78JA7436, 78RTC214). A novel acenaphthylene episulfide is obtained by treatment of the six-membered sulfoxide (71) with acetic anhydride (Scheme 153) (68JA1676), and photolysis of (72) gives a low yield of episulfide (73 Scheme 154) (72JA521). Low yields may be due to the desulfurization of the thiiranes under the reaction conditions. 

The oxidation of Me2S2 in the presence of aromatics with an increased electron density at several carbons, such as acenaphthylene or phenanthrene, and pyridine leads to similar products of vicinal functionalization (Scheme 32) [128]. 

Acenaphthylene reacts with elemental sulfur in DMF at 120°C to give thiophene (Scheme 82) (415) when the reaction was quenched at the early stage, a dihydro-1,4-dithiin, which is a probable intermediate leading to (415), is isolated <89SUL135>. Acenaphthylene also reacts with an S " species, generated by oxidation of a carbon-sulfur electrode, to give (415) in a better yield <94BSF789>. 

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