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. 2014 Jan 8;10:34–114. doi: 10.3762/bjoc.10.6

Table 15.

Examples of 1,2-dioxanes synthesized by co-oxidation of 1,5-dienes and thiols.

Diene 208 Thiol Reaction conditions 1,2-Dioxane 209 Yield, % Reference
graphic file with name Beilstein_J_Org_Chem-10-34-i239.jpg R3SH
R3 = Ph, 4-FC6H4, n-Bu, t-Bu, MeO2CCH2, cyclohexyl, Ph3C		 1) O2, DBPO, benzene/heptane, rt, 10 h or O2, AIBN, hν, MeCN, 4 °C,
10 h
2) Ph3P, CH2Cl2, 0–5 °C, 2 h, rt, 1 h		 graphic file with name Beilstein_J_Org_Chem-10-34-i240.jpg 6–54 [107,179,315]
graphic file with name Beilstein_J_Org_Chem-10-34-i241.jpg PhSH
4-ClC6H4SH		 1) O2, AIBN, hν, MeCN, 0 °C, 2 h
2) Ph3P, CH2Cl2,
0 °C to rt		 graphic file with name Beilstein_J_Org_Chem-10-34-i242.jpg 70 (Ar = Ph),
21 (Ar = 4-ClC6H4)		 [102,316]