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The reaction of sulfur with dilithio compounds. The syntheses and structures of phenanthro [1, 10-cd]-1,2-dithiole and phenanthro[4,5-cde] [1,2]dithiin

✍ Scribed by Arthur J. Ashe III; Jeff W. Kampf; Paresh M. Savla

Publisher: John Wiley and Sons
Year: 1994
Tongue: English
Weight: 561 KB
Volume: 5
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520050206

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✦ Synopsis

The sequential reaction of selected polycyclic aromatic hydrocarbons with butyllithium/TMEDA/ hexane and sulfur allows preparation of ring-fused dithiins, dithioles, and thiophenes. In this manner, phenanthrene has been converted to phenan-

thro[4,5-~de][1,2]dithiin

and phenanthro[l,IOc~-1,2dithiole. Yellow crystals of the dithiin form inoC2/c (#15) space group .with < = 4, a = 13.537(3) A, b = 8.933(2) A, c = 9.601(4) A, and p = 116.19 (2)"; while orange crystals of the dithiob form in P2,2,2, (#19) space groyp with 2 = 4, a 4.1507(5) A, b = 14.436(3) A, and c := 16.972(3) A. Full structures have been determined for both compounds.

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