Reações de ésteres ß,Y-insaturados com tálio(III) e de 1,2-di-hidronaftalenos com iodo(III) / Reactions of ß,Y-unsaturated esters with thallium(III) and 1,2-dihydronaphthalenes with iodine(III)

AUTOR(ES)

Eliane Corrêa Pedrozo

DATA DE PUBLICAÇÃO

2006

RESUMO

This dissertation presents a study about the ring contraction of ß,y-unsaturated esters promoted by thallium trinitrate (TTN) and 1,2-dihydronaphthalenes promoted by hydroxy(tosyloxy)iodobenzene (HTIB). Both studies aimed the synthesis of functionalizated indans. The reaction of a series of ß,y-unsaturad esters with TTN in acetic acid led to the corresponding ring contraction products, giving indans in good yields. The presence of electron donating groups in the 6-position of the aromatic ring increases the yield of the ring contraction product. On the other hand, electron withdrawing groups in the 7-position of the aromatic ring leds to a decrease of the yield of the desired product, when compared to substrates which are not substituted in this position. The increasement of the alkane chain at the alpha-carbonyl position did not interfere in the yield of the ring contraction product. The esters substituted by an alkyl group at 4-position of the ciclohexene ring leads to the ring contraction product, where the trans-1,3-disubstituted indan is the major product. The reaction of 1,2-dihydronaphthalene with HTIB in methanol gave the ring contraction product 1-dimetoxymethyl-indan with moderate yield, together with the addition products cis- and trans-1,2-dimetoxy-1,2,3,4-tetrahydronaphthalene. On the other hand, the reaction of 1,2-dihydronaphthalene with HTIB in acetonitrile, dichloro-methane or trimethyl orthoformate gave the aromatization product (naphthalene). The reaction of 4-methyl-1,2-dihydronaphthalene and 1,4-dimethyl-1,2-dihydronaphthalene with HTIB in acetonitrile leads to ring contraction products 1-indan-1-yl-ethanone and 1-(trans-3-methyl-indan-1-yl)-ethanone, respectively, in good yieds. The reaction of 4-methyl-1,2-dihydronaphthalene with HTIB in methanol gave the addition products cis- and trans-1,2-dimetoxy-1,2,3,4-tetrahydro-1-methyl-naphthalene) with very good yield.

ASSUNTO(S)

dihydronaphthalenes hydroxy(tosyloxy)iodobenzene ring contraction indanes hidroxi(tosiloxi)iodobenzeno Ésteres insaturados indano di-hidronaftalenos unsaturated esters contração de anel

Documentos Relacionados

• Ring Contraction of 1,2-Di-hydronaphthalenes with Iodine(III) and its Application in Total Synthesis of (±)-Indatraline
• Reações de contração de anel promovidas por sais de tálio (III)
• Reações de contração de anel promovidas por sais de tálio(III)
• Complexometric determination of thallium(III) using ethanethiol as a selective masking agent
• Thallium trinitrate-mediated ring contraction of 1,2-dihydronaphthalenes: the effect of electron-donating and electron-withdrawing groups