متیلن‌دار کردن لومباردو

متیلن‌دار کردن لومباردو
نامگذاری شده پس از	لوسیانو لومباردو
نوع واکنش	واکنش‌های اکسایش و کاهش آلی

متیلن‌دار کردن لومباردو یا متیلناسیون لومباردو (به انگلیسی: Lombardo methylenation) یک نام واکنش در شیمی آلی است که امکان متیلن‌دار کردن ترکیبات کربونیل‌دار با استفاده از واکنشگر لومباردو را امکان‌پذیر می‌سازد. این واکنشگر ترکیبی از روی، دی‌برمومتان و تیتانیم تتراکلرید است.^[۱]^[۲]^[۳]^[۴]^[۵]^[۶]^[۷]

کاربردها[ویرایش]

متیلن‌دار کردن لومباردو در سنتز جامع تترودوتوکسین^[۸] و هیروستن استفاده می‌شود.^[۹]^[۱۰]

منابع[ویرایش]

↑ Lombardo, Luciano (1982-07-27). "Methylenation of carbonyl compounds with ZnCH2Br2TiCl4. Application to gibberellins". Tetrahedron Letters. 23 (41): 4293–4296. doi:10.1016/S0040-4039(00)88728-6.
↑ Wang, Zerong (15 September 2010). Comprehensive Organic Name Reactions and Reagents. doi:10.1002/9780470638859.conrr397. ISBN 9780470638859.
↑ Kulinkovich, Oleg G.; Meijere, Armin de (2000-07-21). "1,n-Dicarbanionic Titanium Intermediates from Monocarbanionic Organometallics and Their Application in Organic Synthesis". Chemical Reviews. 100 (8): 2789–2834. doi:10.1021/cr980046z.
↑ Pine, Stanley H. (2004-08-15). "Carbonyl Methylenation and Alkylidenation Using Titanium-Based Reagents". Organic Reactions. doi:10.1002/0471264180.or043.01.
↑ Hartley, Richard C.; Li, Jianfeng; Main, Calver A.; McKiernan, Gordon J. (2007-06-04). "Titanium carbenoid reagents for converting carbonyl groups into alkenes". Tetrahedron. 63 (23): 4825–4864. doi:10.1016/j.tet.2007.03.015.
↑ Luciano Lombardo (1987). "Methylenation of Carbonyl Compounds: (+)-3-Methylene-cis-p-menthane". Organic Syntheses. 65: 81. doi:10.15227/orgsyn.065.0081.
↑ Marsden, Stephen P.; Ducept, Pascal C. (2005). "Synthesis of highly substituted allenylsilanes by alkylidenation of silylketenes". Beilstein Journal of Organic Chemistry. 1 (1): 5. doi:10.1186/1860-5397-1-5. PMC 1399453. PMID 16542018.
↑ Hinman, Andrew; Du Bois, Justin (2003-08-30). "A Stereoselective Synthesis of (−)-Tetrodotoxin". Journal of the American Chemical Society. 125 (38): 11510–11511. doi:10.1021/ja0368305.
↑ Ley, Steven V.; Murray, P. John (1982). "A short syntesis of (±)-hirsutene involving the use of an organoselenium-mediated cyclization reaction". Journal of the Chemical Society, Chemical Communications (21): 1252–1253. doi:10.1039/C39820001252.
↑ Ley, Steven V.; Murray, P. John; Palmer, Brian D. (1985-11-14). "Total synthesis of the sesquiterpene (±)-hirsutene using an organoselenium-mediated cyclization reaction". Tetrahedron. 41 (21): 4765–4769.

[1] Lombardo, Luciano (1982-07-27). "Methylenation of carbonyl compounds with ZnCH2Br2TiCl4. Application to gibberellins". Tetrahedron Letters. 23 (41): 4293–4296. doi:10.1016/S0040-4039(00)88728-6.

[2] Wang, Zerong (15 September 2010). Comprehensive Organic Name Reactions and Reagents. doi:10.1002/9780470638859.conrr397. ISBN 9780470638859.

[3] Kulinkovich, Oleg G.; Meijere, Armin de (2000-07-21). "1,n-Dicarbanionic Titanium Intermediates from Monocarbanionic Organometallics and Their Application in Organic Synthesis". Chemical Reviews. 100 (8): 2789–2834. doi:10.1021/cr980046z.

[4] Pine, Stanley H. (2004-08-15). "Carbonyl Methylenation and Alkylidenation Using Titanium-Based Reagents". Organic Reactions. doi:10.1002/0471264180.or043.01.

[5] Hartley, Richard C.; Li, Jianfeng; Main, Calver A.; McKiernan, Gordon J. (2007-06-04). "Titanium carbenoid reagents for converting carbonyl groups into alkenes". Tetrahedron. 63 (23): 4825–4864. doi:10.1016/j.tet.2007.03.015.

[6] Luciano Lombardo (1987). "Methylenation of Carbonyl Compounds: (+)-3-Methylene-cis-p-menthane". Organic Syntheses. 65: 81. doi:10.15227/orgsyn.065.0081.

[7] Marsden, Stephen P.; Ducept, Pascal C. (2005). "Synthesis of highly substituted allenylsilanes by alkylidenation of silylketenes". Beilstein Journal of Organic Chemistry. 1 (1): 5. doi:10.1186/1860-5397-1-5. PMC 1399453. PMID 16542018.

[8] Hinman, Andrew; Du Bois, Justin (2003-08-30). "A Stereoselective Synthesis of (−)-Tetrodotoxin". Journal of the American Chemical Society. 125 (38): 11510–11511. doi:10.1021/ja0368305.

[9] Ley, Steven V.; Murray, P. John (1982). "A short syntesis of (±)-hirsutene involving the use of an organoselenium-mediated cyclization reaction". Journal of the Chemical Society, Chemical Communications (21): 1252–1253. doi:10.1039/C39820001252.

[10] Ley, Steven V.; Murray, P. John; Palmer, Brian D. (1985-11-14). "Total synthesis of the sesquiterpene (±)-hirsutene using an organoselenium-mediated cyclization reaction". Tetrahedron. 41 (21): 4765–4769.

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