{"id":2581,"date":"2017-11-22T09:27:54","date_gmt":"2017-11-22T12:27:54","guid":{"rendered":"http:\/\/cursos.ufrrj.br\/posgraduacao\/ppgq\/?page_id=2581"},"modified":"2017-11-22T09:27:54","modified_gmt":"2017-11-22T12:27:54","slug":"ic-1324","status":"publish","type":"page","link":"https:\/\/cursos.ufrrj.br\/posgraduacao\/ppgq\/atividades-disciplinares\/ic-1324\/","title":{"rendered":"IC-1324 \u2013 S\u00edntese Org\u00e2nica"},"content":{"rendered":"

4 cr\u00e9ditos \u2013 60 horas te\u00f3ricas<\/strong><\/p>\n

 <\/p>\n

OBJETIVOS<\/strong>:<\/p>\n

Permitir ao aluno o conhecimento e o entendimento dos mecanismos e m\u00e9todos sint\u00e9ticos aplicados \u00e0 qu\u00edmica org\u00e2nica<\/p>\n

 <\/p>\n

EMENTA<\/strong>:<\/p>\n

1. Processos de forma\u00e7\u00e3o de liga\u00e7\u00e3o simples carbono-carbono<\/p>\n

2. Processos de forma\u00e7\u00e3o de liga\u00e7\u00e3o dupla carbono-carbono<\/p>\n

3. Rea\u00e7\u00f5es de Cicloadi\u00e7\u00f5es.<\/p>\n

4. Redu\u00e7\u00e3o<\/p>\n

5. Oxida\u00e7\u00e3o<\/p>\n

6. Grupo de Prote\u00e7\u00e3o<\/p>\n

7. An\u00e1lise Retrossint\u00e9tica<\/p>\n

 <\/p>\n

CONTE\u00daDO PROGRAM\u00c1TICO:<\/strong><\/p>\n

1. Processos de Forma\u00e7\u00e3o de Liga\u00e7\u00f5es Simples Carbono-Carbono<\/em><\/p>\n

Alquila\u00e7\u00e3o de Nucle\u00f3filos de Carbono: Enolatoes e Enaminas.<\/p>\n

Forma\u00e7\u00e3o e import\u00e2ncia do \u00edon enolato; alquila\u00e7\u00e3o de alde\u00eddos, cetonas, \u00e9steres, amidas e nitrilas;<\/p>\n

alquila\u00e7ao de compostos 1,3-dicarbon\u00edlicos.<\/p>\n

Enaminas e Iminas: prepara\u00e7\u00e3o, enaminas como reagente de Michael. Carboxila\u00e7\u00e3o de carboc\u00e1tions.<\/p>\n

Rea\u00e7\u00f5es de condensa\u00e7\u00e3o: Condensa\u00e7\u00e3o Ald\u00f3lica; Anela\u00e7\u00e3o de Robinson, Claisen-Schmidt,<\/p>\n

Knoevenagel, Mannich e Reformatsky.<\/p>\n

Aplica\u00e7\u00f5es sint\u00e9ticas de organomet\u00e1licos: Organol\u00edtio, Organocupratos e Organomagn\u00e9sios-<\/p>\n

Reagente de Grignard. Outros processos.<\/p>\n

 <\/p>\n

2. Processos de Forma\u00e7\u00e3o de Liga\u00e7\u00f5es Duplas Carbono-Carbono<\/em><\/p>\n

Rea\u00e7\u00f5es de beta-elimina\u00e7ao. Elimina\u00e7\u00f5es pirol\u00edticas. Descarboxila\u00e7\u00e3o oxidativa de \u00e1cidos<\/p>\n

carbox\u00edlicos; descarboxila\u00e7\u00e3o de beta-lactonas. Rea\u00e7\u00f5es de Wittig e relacionadas. S\u00edntese de<\/p>\n

alquenos tri- e tetra-substitu\u00eddos. Rea\u00e7\u00f5es de fragmenta\u00e7\u00e3o. Rearranjos: Claisen, Sulf\u00f3xidos. Outros<\/p>\n

processos.<\/p>\n

 <\/p>\n

3. Rea\u00e7\u00f5es de Cicloadi\u00e7\u00f5es<\/em><\/p>\n

Rea\u00e7\u00e3o de Diels-Alder: processo geral, dieno e dien\u00f3lfilo.<\/p>\n

Rea\u00e7\u00e3o Diels-Alder Intramolecular e retro-Diels-Alder. Estereoqu\u00edmica, regioqu\u00edmica e Diels-Alder<\/p>\n

Assim\u00e9trica. Rea\u00e7\u00f5es 1,3-dipolar.<\/p>\n

 <\/p>\n

4. Redu\u00e7\u00e3o<\/em><\/p>\n

Hidrogen\u00e7\u00e3o catal\u00edtica: catalisadores; seletividade da redu\u00e7\u00e3o; redu\u00e7\u00e3o de grupos funcionais;<\/p>\n

estereoqu\u00edmica e mecanismo; hidrogena\u00e7\u00e3o homog\u00eanea, hidrogen\u00f3lise. Redu\u00e7\u00e3o por metais em<\/p>\n

solu\u00e7\u00e3o: metais em meio \u00e1cido; redu\u00e7\u00e3o de subst\u00e2ncias carbon\u00edlicas, metais em meio alco\u00f3licos;<\/p>\n

metal em am\u00f4nia l\u00edquida. (Redu\u00e7\u00e3o de Birch). Redu\u00e7\u00e3o com reagentes transferidores de hidreto:<\/p>\n

hidreto de l\u00edtio e alum\u00ednio, boroidreto de s\u00f3dio; alc\u00f3xidos de alum\u00edmio, hidretos de diisobutil<\/p>\n

alum\u00ednio; cianoboridreto de s\u00f3dio e trialquilboroidretos. Redu\u00e7\u00e3o com boranos. Outros m\u00e9todos:<\/p>\n

Wolff-Kishner, desulfuriza\u00e7\u00e3o de tiocetais, redu\u00e7\u00e3o com tit\u00e2nio.<\/p>\n

 <\/p>\n

5. Oxida\u00e7\u00e3o<\/em><\/p>\n

Oxida\u00e7\u00e3o de hidrocarbonetos. Oxida\u00e7\u00e3o de \u00e1lcool: com compostos de cromo e mangan\u00eas. Oxida\u00e7\u00e3o<\/p>\n

de liga\u00e7\u00f5es duplas carbono-carbono: di\u00f3is, ep\u00f3xidos com per\u00e1cidos e per\u00e9ster, epoxida\u00e7\u00e3o de<\/p>\n

Sharpless, ozon\u00f3lises. Oxida\u00e7\u00e3o de cetona: forma\u00e7\u00e3o de cetonas \u03b1,\u03b2-insaturadas, oxida\u00e7\u00e3o de<\/p>\n

Bayer-Villiger. Oxida\u00e7\u00f5es com per\u00f3xidos de n\u00edquel. Oxida\u00e7\u00f5es com tetr\u00f3xido de rut\u00eanio. Oxida\u00e7\u00e3o<\/p>\n

com di\u00f3xido de sel\u00eanio. Oxida\u00e7\u00e3o de aminas; oxida\u00e7\u00e3o de liga\u00e7\u00f5es al\u00edlicas carbono-hidrog\u00eanio.<\/p>\n

 <\/p>\n

6. Grupo de Prote\u00e7\u00e3o<\/em><\/p>\n

O uso de grupos de prote\u00e7\u00e3o em s\u00edntese org\u00e2nica. Grupo de prote\u00e7\u00e3o para \u00e1lcool. Grupo de<\/p>\n

prote\u00e7\u00e3o para fenol. Grupo de prote\u00e7\u00e3o para subst\u00e2ncias carbon\u00edlicas. Grupo de prote\u00e7\u00e3o para<\/p>\n

aminas e amidas. Reagentes usados para desprote\u00e7\u00e3o.<\/p>\n

 <\/p>\n

7. An\u00e1lise Retrossint\u00e9tica<\/em><\/p>\n

Desconex\u00e3o simples das liga\u00e7\u00f5es. Equivalentes sint\u00e9ticos. Conceito de \u201csynthons\u201d. Interconvers\u00e3o<\/p>\n

de Grupo funcional ( FGI). Estrat\u00e9gia e planejamento de uma rota sint\u00e9tica. Exemplos pr\u00e1ticos.<\/p>\n

 <\/p>\n

BIBLIOGRAFIA<\/strong>:<\/p>\n

1. J. March, \u201cAdvance Organic Chemistry\u201d, 3a. ed., Wiley, New York (1992).<\/p>\n

2. F. A. Carey and R. J. Sundberg, \u201cAdvance Organic Chemistry\u201d, Vol. 1. e 2, 2a. Ed., Plenum Press,<\/p>\n

New York, (1993).<\/p>\n

3. W. Carruthers, \u201cSome Modern Methods of Organic Synthesis\u201d 3a. Ed., Cambridge Press, London<\/p>\n

(1987).<\/p>\n

4. B. Mundy, \u201cConcepts of Organic Synthesis\u201d, Marcel Dekker, New York (1979).<\/p>\n

5. H. O. House, \u201cModern Synthetic Reactions \u201c Benjamin, Menlo Park, Calif. (1972).<\/p>\n

6. J.C. Stowell, \u201cCarbocations in Synthesis\u201d, Wiley, New York (1979)<\/p>\n

7. S. Warren, \u201cOrganic Synthesis: The Disconnections Approach\u201d, Wiley, New York (1983).<\/p>\n

8. M. B. Smith. \u201cOrganic Synthesis\u201d, Mc Graw Hill, New York (2002).<\/p>\n

9. S. Warren, \u201cWorkbook for Organic Synthesis: The Disconnections Approach\u201d, Wiley, New York<\/p>\n

(1985).<\/p>\n

10. Willis e M. Wills. \u201cOrganic Synthesis\u201d. Oxford Chemistry Primers. Oxford. New York. 1995.<\/p>\n

11. Mil\u00f5s Hudlicky, \u201cReductions in Organic Chemistry\u201d, 2a. ed, ACS Monograph 188, Washington,<\/p>\n

(1996).<\/p>\n

12. M. Hudlicky, \u201cOxidation in Organic Chemistry\u201d, ACS Monograph 186, Washington, (1996).<\/p>\n","protected":false},"excerpt":{"rendered":"

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