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url url url url
  2. Weltenzyklopädie
  3. همولوگ‌شدن سیفرت–گیلبرت - ویکی‌پدیا، دانشنامهٔ آزاد
همولوگ‌شدن سیفرت–گیلبرت - ویکی‌پدیا، دانشنامهٔ آزاد
از ویکی‌پدیا، دانشنامهٔ آزاد
همولوگ‌شدن سیفرت–گیلبرت
نامگذاری شده پس از دیتمار سیفرت
جان سی. گیلبرت
نوع واکنش واکنش همولوگ‌شدن
شناسه‌ها
در درگاه شیمی آلی seyferth-gilbert-homologation
RSC ontology ID RXNO:0000387

همولوگ‌شدن یا همولوگاسیون سیفرت–گیلبرت(به انگلیسی: Seyferth–Gilbert homologation) یک واکنش شیمیایی بین یک آریل کتون 1 (یا آلدهید) با دی‌متیل‌(دی‌آزومتیل)‌فسفونات 2 و پتاسیم ترت-بوتواکسید برای ایجاد آلکین‌های استخلافی 3 است.[۱][۲] دی‌متیل‌(دی‌آزومتیل)‌فسفونات 2 اغلب واکنشگر سیفرت–گیلبرت نامیده می شود.[۳]

The Seyferth–Gilbert homologation
همسان سازی سیفرث-گیلبرت

به این واکنش‌ها همولوگ‌شدن یا همولوگاسیون گفته می شود زیرا محصول دقیقاً یک کربن بیشتر از ماده اولیه دارد.

سازوکار واکنش

پروتون‌زدایی واکنشگر سیفرت–گیلبرت A یک آنیون B ایجاد می کند که با کتون واکنش می دهد و اگزافسفتان D را تشکیل می دهد. حذف دی‌متیل‌فسفات E وینیل دی‌آزو میانی Fa و Fb را می دهد. تولید گاز نیتروژن یک وینیل کاربن G می دهد که از طریق مهاجرت-۲٬۱ آلکین H مورد نظر را تشکیل می دهد.

The mechanism of the Seyferth–Gilbert homologation
مکانیسم همسان سازی سیفرث-گیلبرت

همچنین ببینید

منابع

  1. ↑ D. Seyferth; R. S. Marmor; P. Hilbert (1971). "Reactions of dimethylphosphono-substituted diazoalkanes. (MeO)2P(O)CR transfer to olefins and 1,3-dipolar additions of (MeO)2P(O)C(N2)R". J. Org. Chem. 36 (10): 1379–1386. doi:10.1021/jo00809a014.
  2. ↑ J. C. Gilbert; U. Weerasooriya (1982). "Diazoethenes: their attempted synthesis from aldehydes and aromatic ketones by way of the Horner-Emmons modification of the Wittig reaction. A facile synthesis of alkynes". J. Org. Chem. 47 (10): 1837–1845. doi:10.1021/jo00349a007.
  3. ↑ D. G. Brown; E. J. Velthuisen; J. R. Commerford; R. G. Brisbois; T. H. Hoye (1996). "A Convenient Synthesis of Dimethyl (Diazomethyl)phosphonate (Seyferth/Gilbert Reagent)". J. Org. Chem. 61 (7): 2540–2541. doi:10.1021/jo951944n.
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