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Simmons-Smith Cyclopropanation

Included in Reactions.

Addition

Source Details

Id

simmons-smith

Name
{
  "en": "Simmons-Smith Cyclopropanation",
  "ar": "Simmons-Smith Cyclopropanation",
  "cs": "Simmons-Smithova cyklopropanace",
  "da": "Simmons-Smith-cyclopropanering",
  "de": "Simmons-Smith-Cyclopropanierung",
  "el": "Κυκλοπροπανίωση Simmσεs-Smith",
  "es-419": "Cyclopropanation de Simmons-Smith",
  "es-ES": "Cyclopropanation de Simmons-Smith",
  "es": "Cyclopropanation de Simmons-Smith",
  "fi": "Simmons-Smith-syklopropanointi",
  "fr": "Cyclopropanation de Simmons-Smith",
  "he": "Simmons-Smith Cyclopropanation",
  "hr": "Simmons-Smithova ciklopropanacija",
  "hu": "Simmons-Smith ciklopropanálás",
  "id": "Siklopropanasi Simmons-Smith",
  "it": "Cyclopropanation di Simmons-Smith",
  "ja": "Simmons-Smithシクロプロパン化",
  "ko": "Simmons-Smith 사이클로프로판화",
  "lv": "Simmonsa-Smita ciklopropanēšana",
  "nb": "Simmons-Smith-syklopropanering",
  "nl": "Simmons-Smith-cyclopropanatie",
  "pl": "Cyklopropanowanie Simmonsa-Smitha",
  "pt-BR": "Cyclopropanation de Simmons-Smith",
  "pt-PT": "Cyclopropanation de Simmons-Smith",
  "ro": "Cyclopropanation de Simmons-Smith",
  "ru": "Циклопропанирование Симмонса-Смита",
  "sk": "Simmons-Smithova cyklopropanácia",
  "sl": "Simmons-Smithova ciklopropanacija",
  "sv": "Simmons-Smith-cyklopropanering",
  "th": "ไซโคลโพรพาเนชันแบบ Simmons-Smith",
  "tr": "Simmüzerindes-Smith siklopropanolarakyüzerindeu",
  "uk": "Циклопропанування Сіммонса-Сміта",
  "vi": "Cyclopropan hóa Simmons-Smith",
  "zh-Hans": "Simmons-Smith 环丙烷化",
  "zh": "Simmons-Smith 环丙烷化"
}
Type
{
  "en": "Addition",
  "ar": "إضافة",
  "cs": "Adice",
  "da": "Addition",
  "de": "Addition",
  "el": "Προσθήκη",
  "es-419": "Adición",
  "es-ES": "Adición",
  "es": "Adición",
  "fi": "Additio",
  "fr": "Addition",
  "he": "סיפוח",
  "hr": "Adicija",
  "hu": "Addíció",
  "id": "Adisi",
  "it": "Addizione",
  "ja": "付加",
  "ko": "첨가",
  "lv": "Pievienošana",
  "nb": "Addisjon",
  "nl": "Additie",
  "pl": "Addycja",
  "pt-BR": "Adição",
  "pt-PT": "Adição",
  "ro": "Adiție",
  "ru": "Присоединение",
  "sk": "Adícia",
  "sl": "Adicija",
  "sv": "Addition",
  "th": "การเติม",
  "tr": "Katılma",
  "uk": "Приєднання",
  "vi": "Cộng",
  "zh-Hans": "加成",
  "zh": "加成"
}
Starting Material

CC=CC

Product

CC1CC1C

Reagents

CH₂I₂, Zn-Cu couple (or Et₂Zn)

Mechanism
[
  {
    "smiles": "CC=CC",
    "description": {
      "en": "2-Butene (alkene substrate)",
      "ar": "2-بيوتين (ألكين ركيزة)",
      "cs": "2-Buten (alken substrat)",
      "da": "2-Butene (alken substrat)",
      "de": "2-Butene (Alken Substrat)",
      "el": "2-Butene (αλκένιο υπόστρωμα)",
      "es-419": "2-Butene (alqueno sustrato)",
      "es-ES": "2-Butene (alqueno sustrato)",
      "es": "2-Butene (alqueno sustrato)",
      "fi": "2-Butene (alkeeni substraatti)",
      "fr": "2-Butene (alcène substrat)",
      "he": "2-בוטן (אלקן סובסטרט)",
      "hr": "2-Buten (alken supstrat)",
      "hu": "2-Butene (alkén szubsztrát)",
      "id": "2-Butena (substrat alkena)",
      "it": "2-Butene (alchene substrato)",
      "ja": "2-ブテン(アルケン基質)",
      "ko": "2-뷰텐(알켄 기질)",
      "lv": "2-Butens (alkens substrats)",
      "nb": "2-Butene (alken substrat)",
      "nl": "2-Butene (alkeen substraat)",
      "pl": "2-Buten (alken substrat)",
      "pt-BR": "2-Butene (alceno substrato)",
      "pt-PT": "2-Butene (alceno substrato)",
      "ro": "2-Butene (alchenă substrat)",
      "ru": "2-Бутен (алкен субстрат)",
      "sk": "2-Buten (alken substrat)",
      "sl": "2-Buten (alken substrat)",
      "sv": "2-Butene (alken substrat)",
      "th": "2-บิวทีน (สารตั้งต้นแอลคีน)",
      "tr": "2-Butene (alken substrde)",
      "uk": "2-Бутен (алкен субстрат)",
      "vi": "2-buten (cơ chất anken)",
      "zh-Hans": "2-丁烯(烯烃底物)",
      "zh": "2-丁烯(烯烃底物)"
    }
  },
  {
    "smiles": "CC1CC1C",
    "description": {
      "en": "CH₂ delivered to same face (syn addition) → cyclopropane",
      "ar": "CH₂ delivered إلى الوجه نفسه (syn إضافة) → cyclopropane",
      "cs": "CH₂ delivered na stejne strany (syn adice) → cyclopropane",
      "da": "CH₂ delivered til same face (syn addition) → cyclopropane",
      "de": "CH₂ delivered zu same face (syn addition) → cyclopropane",
      "el": "CH₂ delivered σε same face (syn προσθήκη) → cyclopropane",
      "es-419": "CH₂ delivered a misma cara (syn adición) → cyclopropane",
      "es-ES": "CH₂ delivered a misma cara (syn adición) → cyclopropane",
      "es": "CH₂ delivered a misma cara (syn adición) → cyclopropane",
      "fi": "CH₂ delivered kohti same face (syn addition) → cyclopropane",
      "fr": "CH₂ delivered en même face (syn addition) → cyclopropane",
      "he": "CH₂ delivered ל אותו פנים (syn סיפוח) → cyclopropane",
      "hr": "CH₂ delivered u iste strane (syn adicija) → cyclopropane",
      "hu": "CH₂ delivered to same face (syn addíció) → cyclopropane",
      "id": "CH₂ dikirim ke sisi yang sama (adisi syn) → siklopropana",
      "it": "CH₂ delivered a stessa faccia (syn addizione) → cyclopropane",
      "ja": "CH₂が同じ面に供与される(syn付加)→ シクロプロパン",
      "ko": "CH₂가 같은 면으로 전달됨(syn 첨가) → 사이클로프로판",
      "lv": "CH₂ delivered uz tas pasas puses (syn pievienosana) → cyclopropane",
      "nb": "CH₂ delivered til same face (syn addition) → cyclopropane",
      "nl": "CH₂ delivered tot same face (syn addition) → cyclopropane",
      "pl": "CH₂ delivered do tej samej strony (syn addycja) → cyclopropane",
      "pt-BR": "CH₂ delivered a mesma face (syn adição) → cyclopropane",
      "pt-PT": "CH₂ delivered a mesma face (syn adição) → cyclopropane",
      "ro": "CH₂ delivered la aceeași față (syn adiție) → cyclopropane",
      "ru": "CH₂ delivered в той же стороны (syn присоединение) → cyclopropane",
      "sk": "CH₂ delivered na tej istej strany (syn adicia) → cyclopropane",
      "sl": "CH₂ delivered v iste strani (syn adicija) → cyclopropane",
      "sv": "CH₂ delivered till same face (syn addition) → cyclopropane",
      "th": "CH₂ ถูกส่งไปยังด้านเดียวกัน (การเติมแบบ syn) → ไซโคลโพรเพน",
      "tr": "CH₂ delivered to same face (syn kdeılma) → cyclopropane",
      "uk": "CH₂ delivered до того самого боку (syn приєднання) → cyclopropane",
      "vi": "CH₂ được đưa vào cùng một mặt (cộng syn) → cyclopropane",
      "zh-Hans": "CH₂ 传递到同一面(syn 加成)→ 环丙烷",
      "zh": "CH₂ 传递到同一面(syn 加成)→ 环丙烷"
    }
  }
]
Stereochemistry
{
  "en": "Syn addition - cyclopropane stereochemistry reflects alkene geometry",
  "ar": "syn إضافة - cyclopropane كيمياء فراغية reflects ألكين هندسة",
  "cs": "Syn adice - cyclopropane stereochemie reflects alken geometry",
  "da": "syn-addition - cyclopropane stereokemi reflects alken geometry",
  "de": "Syn-Addition - cyclopropane Stereochemie reflects Alken geometry",
  "el": "Syn προσθήκη - cyclopropane στερεοχημεία reflects αλκένιο geometry",
  "es-419": "Syn adición - cyclopropane estereoquímica reflects alqueno geometry",
  "es-ES": "Syn adición - cyclopropane estereoquímica reflects alqueno geometry",
  "es": "Syn adición - cyclopropane estereoquímica reflects alqueno geometry",
  "fi": "syn-additio - cyclopropane stereokemia reflects alkeeni geometry",
  "fr": "Syn addition - cyclopropane stéréochimie reflects alcène geometry",
  "he": "syn סיפוח - cyclopropane סטריאוכימיה reflects אלקן גאומטריה",
  "hr": "Syn adicija - cyclopropane stereokemija reflects alken geometry",
  "hu": "Syn addíció - cyclopropane sztereokémia reflects alkén geometry",
  "id": "Adisi syn - stereokimia siklopropana mencerminkan geometri alkena",
  "it": "Syn addizione - cyclopropane stereochimica reflects alchene geometry",
  "ja": "syn付加 - シクロプロパンの立体化学はアルケンの幾何を反映する",
  "ko": "syn 첨가 - 사이클로프로판의 입체화학은 알켄 기하를 반영함",
  "lv": "Syn pievienosana - cyclopropane stereokimija reflects alkens geometry",
  "nb": "syn-addisjon - cyclopropane stereokjemi reflects alken geometry",
  "nl": "syn-additie - cyclopropane stereochemie reflects alkeen geometry",
  "pl": "Syn addycja - cyclopropane stereochemia reflects alken geometry",
  "pt-BR": "Syn adição - cyclopropane estereoquímica reflects alceno geometry",
  "pt-PT": "Syn adição - cyclopropane estereoquímica reflects alceno geometry",
  "ro": "Syn adiție - cyclopropane stereochimie reflects alchenă geometry",
  "ru": "Syn присоединение - cyclopropane стереохимия reflects алкен geometry",
  "sk": "Syn adicia - cyclopropane stereochemia reflects alken geometry",
  "sl": "Syn adicija - cyclopropane stereokemija reflects alken geometry",
  "sv": "syn-addition - cyclopropane stereokemi reflects alken geometry",
  "th": "การเติมแบบ syn - สเตอริโอเคมีของไซโคลโพรเพนสะท้อนเรขาคณิตของแอลคีน",
  "tr": "Syn kdeılma - cyclopropane stereokimya reflects alken geometry",
  "uk": "Syn приєднання - cyclopropane стереохімія reflects алкен geometry",
  "vi": "Cộng syn - hóa lập thể của cyclopropane phản ánh hình học anken",
  "zh-Hans": "syn 加成 - 环丙烷立体化学反映烯烃几何构型",
  "zh": "syn 加成 - 环丙烷立体化学反映烯烃几何构型"
}
Tips
[
  {
    "en": "Alkene → Cyclopropane",
    "ar": "ألكين → Cyclopropane",
    "cs": "Alken → Cyclopropane",
    "da": "Alken → Cyclopropane",
    "de": "Alken → Cyclopropane",
    "el": "Αλκένιο → Cyclopropane",
    "es-419": "Alqueno → Cyclopropane",
    "es-ES": "Alqueno → Cyclopropane",
    "es": "Alqueno → Cyclopropane",
    "fi": "Alkeeni → Cyclopropane",
    "fr": "Alcène → Cyclopropane",
    "he": "אלקן → Cyclopropane",
    "hr": "Alken → Cyclopropane",
    "hu": "Alkén → Cyclopropane",
    "id": "Alkena → Siklopropana",
    "it": "Alchene → Cyclopropane",
    "ja": "アルケン → シクロプロパン",
    "ko": "알켄 → 사이클로프로판",
    "lv": "Alkens → Cyclopropane",
    "nb": "Alken → Cyclopropane",
    "nl": "Alkeen → Cyclopropane",
    "pl": "Alken → Cyclopropane",
    "pt-BR": "Alceno → Cyclopropane",
    "pt-PT": "Alceno → Cyclopropane",
    "ro": "Alchenă → Cyclopropane",
    "ru": "Алкен → Cyclopropane",
    "sk": "Alken → Cyclopropane",
    "sl": "Alken → Cyclopropane",
    "sv": "Alken → Cyclopropane",
    "th": "แอลคีน → ไซโคลโพรเพน",
    "tr": "Alken → Cyclopropane",
    "uk": "Алкен → Cyclopropane",
    "vi": "Anken → cyclopropane",
    "zh-Hans": "烯烃 → 环丙烷",
    "zh": "烯烃 → 环丙烷"
  },
  {
    "en": "Delivers :CH₂ (carbene equivalent)",
    "ar": "Delivers :CH₂ (carbene مكافئ)",
    "cs": "Dodává :CH₂ (karbenový ekvivalent)",
    "da": "Leverer :CH₂ (carbenækvivalent)",
    "de": "Liefert :CH₂ (Carbenäquivalent)",
    "el": "Delivers :CH₂ (carbene equivalent)",
    "es-419": "Entrega :CH₂ (equivalente de carbeno)",
    "es-ES": "Entrega :CH₂ (equivalente de carbeno)",
    "es": "Entrega :CH₂ (equivalente de carbeno)",
    "fi": "Tuottaa :CH₂:n (karbeeniekvivalentti)",
    "fr": "Apporte :CH₂ (équivalent carbène)",
    "he": "Delivers :CH₂ (carbene שקול)",
    "hr": "Dovodi :CH₂ (ekvivalent karbena)",
    "hu": "Delivers :CH₂ (carbene equivalent)",
    "id": "Mengirim :CH₂ (ekuivalen karbena)",
    "it": "Fornisce :CH₂ (equivalente carbenico)",
    "ja": ":CH₂(カルベン等価体)を供与する",
    "ko": ":CH₂(카벤 등가체)를 전달함",
    "lv": "Piegādā :CH₂ (karbēna ekvivalents)",
    "nb": "Leverer :CH₂ (karbenekvivalent)",
    "nl": "Levert :CH₂ (carbeen-equivalent)",
    "pl": "Dostarcza :CH₂ (ekwiwalent karbenu)",
    "pt-BR": "Fornece :CH₂ (equivalente de carbeno)",
    "pt-PT": "Fornece :CH₂ (equivalente de carbeno)",
    "ro": "Livrează :CH₂ (echivalent de carbenă)",
    "ru": "Доставляет :CH₂ (эквивалент карбена)",
    "sk": "Dodáva :CH₂ (karbénový ekvivalent)",
    "sl": "Dostavi :CH₂ (ekvivalent karbena)",
    "sv": "Levererar :CH₂ (karbenekvivalent)",
    "th": "ส่ง :CH₂ (เทียบเท่าคาร์บีน)",
    "tr": "Delivers :CH₂ (carbene equivalent)",
    "uk": "Доставляє :CH₂ (еквівалент карбену)",
    "vi": "Cung cấp :CH₂ (tương đương carbene)",
    "zh-Hans": "递送 :CH₂(卡宾等价体)",
    "zh": "递送 :CH₂(卡宾等价体)"
  },
  {
    "en": "Stereospecific: cis-alkene → cis-disubstituted cyclopropane",
    "ar": "Stereospecific: ألكين cis → cis-disubstituted cyclopropane",
    "cs": "Stereospecific: cis-alken → cis-disubstituted cyclopropane",
    "da": "Stereospecific: cis-alken → cis-disubstitueret cyclopropane",
    "de": "Stereospecific: cis-Alken → cis-disubstituiert cyclopropane",
    "el": "Stereospecific: cis-αλκένιο → cis-disubstituted cyclopropane",
    "es-419": "Stereospecific: cis-alqueno → cis-disubstituted cyclopropane",
    "es-ES": "Stereospecific: cis-alqueno → cis-disubstituted cyclopropane",
    "es": "Stereospecific: cis-alqueno → cis-disubstituted cyclopropane",
    "fi": "Stereospecific: cis-alkeeni → cis-disubstituoitu cyclopropane",
    "fr": "Stereospecific: cis-alcène → cis-disubstituted cyclopropane",
    "he": "Stereospecific: אלקן cis → cis-disubstituted cyclopropane",
    "hr": "Stereospecific: cis-alken → cis-disubstituted cyclopropane",
    "hu": "Stereospecific: cis-alkén → cis-disubstituted cyclopropane",
    "id": "Stereospesifik: cis-alkena → siklopropana cis-disubstitusi",
    "it": "Stereospecific: cis-alchene → cis-disubstituted cyclopro...
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Is Free

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