Octet / Reactions
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...Related Reactions
epoxidation
Is Free
false