Photolysis, thermal decomposition, and oxidation of naphtho[1,8-de]-1,2,3-thiadiazine. Efficient synthesis of naphtho[1,8-bc]thiete and the corresponding sulfoxide and sulfone
Photolysis, thermal decomposition, and oxidation of naphtho[1,8-de]-1,2,3-thiadiazine. Efficient synthesis of naphtho[1,8-bc]thiete and the corresponding sulfoxide and sulfone
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萘并[1,8-de]-1,2,3-噻二嗪的光解、热分解和氧化。
DOI：
10.1021/ja00520a010
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发表时间：
1979
影响因子：
15
通讯作者：
M. Hoshino
中科院分区：
文献类型：
--
作者：
J. Nakayama;T. Fukushima;Etsuro Seki;M. Hoshino
用丙酮、乙腈、苯和甲醇溶液辐照萘[1,8 -ti/e]- 1,2,3 -噻二嗪(4)定量制备萘[1,8 -i> - c]硫醚(7)，用二硫化碳溶液辐照得到萘[1,8 -< fe]- 2,4 -二氢- 1,3 -二硫-2-硫酮(9)（22%）和7（52%）。4在二（乙二醇）乙醚155 C中热分解也主要得到7，而在二硫化碳中分解得到9（50%）和萘[1,8 -«/]-！， 2-二噻唑（10）（11%）。在二硫化碳中辐照或加热时，7发生四元环的碳硫键均裂，最终产物为9，产率低。用等量的间氯过氧苯甲酸氧化4得到71%的萘[1,8 -6c] 1-氧化物（16）和4%的萘[1,8 -¿> c] 1-氧化物（17），而用3 M量的间氯过氧苯甲酸氧化仅得到17，产率为93%。
Naphtho [1, 8-i> c] thiete (7) was prepared quantitatively by irradiation of acetone, acetonitrile, benzene, and methanol solutions of naphtho [l, 8-ti/e]-l, 2, 3-thiadiazine (4), Irradiation of a carbon disulfide solution, on the other hand, gave na-phtho [1, 8-< fe]-2, 4-dihydro-1, 3-dithiin-2-thione (9)(22%) in addition to 7 (52%). Thermal decomposition of 4 in di (ethylene glycol) diethyl etherat 155 C also yielded mainly 7, while decomposition in carbon disulfide gave 9 (50%) and naphtho [1, 8-«/]-!, 2-dithiole (10)(11%). On irradiation or heating in carbon disulfide, 7 undergoes homolytic carbon-sulfur bond cleavage of the four-membered ring to yield 9 as the final productin a low yield. Oxidationof 4 with an equivalent of m-chloroperoxy-benzoic acid gave 71% of naphtho [1, 8-6c] thiete 1-oxide (16) and 4% of naphtho [1, 8-¿> c] thiete 1, 1-dioxide (17), while oxida-tion with 3 M amounts of m-chloroperoxybenzoic acid gave only 17 in 93% yield.