Wittig Reaction

Mechanism of the Wittig Reaction

Reference

Original reference	Chem. Ber. 1954, 87, 13,18.
Wikipedia	link
Organic chemistry portal	link

Sample reactions

This step is from the synthesis of Quinine by Gilbert Stork. Show me the full synthesis.

Ph₃P⁺CH₂OMe Cl^-, TMS₂NK

THF
-78 °C to RT, ON
75 % (2 steps)

This step is from the synthesis of Quinine by Gilbert Stork. Show me the full synthesis.

Ph₃P

THF
Reflux, 3 h
81%

This step is from the synthesis of Quinine by Eric N. Jacobsen. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, KOt-Bu

THF
0 °C to RT, 13 h
73 % (2 steps)

This step is from the synthesis of Prostaglandin F2α by Elias J. Corey. Show me the full synthesis.

Dimsyl sodium

DMSO
80 % (3 steps)

This step is from the synthesis of Prostaglandin F2α by Robert B. Woodward. Show me the full synthesis.

DME
Reflux
79 %

This step is from the synthesis of Strychnine by Larry E. Overman. Show me the full synthesis.

Ph₃P=CH₂

THF
0 °C to RT
92 %

This step is from the synthesis of Gelsemine by Larry E. Overman. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, n-BuLi

THF
-78 °C to RT, 3.5 h
95 %

This step is from the synthesis of Pentacycloanammoxic Acid by Elias J. Corey. Show me the full synthesis.

i-Pr₂NLi, Ph₃P(CH₂)₆CO₂H⁺ Br^-

THF
-78 °C to RT, 7.5 h
67 %

This step is from the synthesis of Sarain A by Larry E. Overman. Show me the full synthesis.

Ph₃P⁺CH₂O(CH₂)₂TMS Cl^-, TMS₂NK

THF
-78 °C to RT, 45 min

This step is from the synthesis of Sarain A by Larry E. Overman. Show me the full synthesis.

TMS₂NNa

DME
-78 to 0 °C, 85 min
76 % (2 steps)

This step is from the synthesis of Malayamycin A by Stephen Hanessian. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, TMS₂NNa

THF
36 % (2 steps)

This step is from the synthesis of Modhephene by Viresh H. Rawal. Show me the full synthesis.

Ph₃P=CH₂

THF
85 % (2 steps)

This step is from the synthesis of Cristatic Acid, Methyl Ester by Alois Fürstner. Show me the full synthesis.

Ph₃P=CMe₂

THF
0 °C, 14 h
57 % (3 steps)

This step is from the synthesis of Indolizidine 223A by Dawei Ma. Show me the full synthesis.

Ph₃P⁺CH₃ I^-, TMS₂NNa

THF
-78 to 0 °C, 90 min

This step is from the synthesis of Taxol by Samuel J. Danishefsky. Show me the full synthesis.

Ph₃P=CH₂

THF
-78 to 0 °C, 25 min
77 %

This step is from the synthesis of Taxol by Paul A. Wender. Show me the full synthesis.

TMS₂NK, Ph₃P⁺CH₂OMe Cl^-

THF
-78 °C to RT, 85 min
91 %

This step is from the synthesis of Fredericamycin A by Dale L. Boger. Show me the full synthesis.

n-BuLi

THF
-78 °C to RT, ON
89 %

This step is from the synthesis of Cyanocobalamin by Robert B. Woodward. Show me the full synthesis.

This step is from the synthesis of Gymnomitrol by George Büchi. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, n-BuLi

THF, DMSO
80 °C, 3.5 h

This step is from the synthesis of Gymnomitrol by Steven C. Welch. Show me the full synthesis.

Ph₃P=CH₂

DMSO
75 °C, 16 h

This step is from the synthesis of Murrayazoline by Noritaka Chida. Show me the full synthesis.

TMS₂NK, Ph₃P⁺CH₂OMe Cl^-

PhMe
0 to 120 °C, 4 h

This step is from the synthesis of Epolactaene by Yujiro Hayashi. Show me the full synthesis.

PhH
90 °C, 90 min
98 %

This step is from the synthesis of Aigialomycin D by Joanne E. Harvey. Show me the full synthesis.

MeOH
0 °C to RT, 12 h
74 % (2 steps)

This step is from the synthesis of Okilactomycin by Amos B. Smith, III. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, n-BuLi

THF
0 °C, 3 h
96 %

This step is from the synthesis of Buckminsterfullerene by Lawrence T. Scott. Show me the full synthesis.

LiOEt

EtOH, CH₂Cl₂
71 % (2 steps)

This step is from the synthesis of Solandelactone E by Varinder K. Aggarwal. Show me the full synthesis.

TMS₂NNa

THF
-78 °C to RT, ON
59 % (2 steps)

This step is from the synthesis of Solandelactone E by Varinder K. Aggarwal. Show me the full synthesis.

TMS₂NNa

THF
-78 °C to RT, ON
80 % (2 steps)

This step is from the synthesis of Doliculide by Arun K. Ghosh. Show me the full synthesis.

PhH
80 °C, 15 h
81 % (2 steps)

This step is from the synthesis of Laurenene by Michael T. Crimmins. Show me the full synthesis.

CH₂Cl₂
40 °C, 60 min
89 % (3 steps)

This step is from the synthesis of Ammosamide B by William Fenical. Show me the full synthesis.

CH₂Cl₂
3.5 h
86 %

This step is from the synthesis of Longifolene by Elias J. Corey. Show me the full synthesis.

n-BuLi

Et₂O, THF
RT to Reflux, 2 d
96 %

This step is from the synthesis of Longifolene by Wolfgang Oppolzer. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, NaOt-Amyl

PhMe
RT, 90 min
88 %

This step is from the synthesis of Nominine by David Y. Gin. Show me the full synthesis.

n-Bu₃P, NaBH(OAc)₃

CH₂Cl₂
RT, 17 h
79 %

This step is from the synthesis of Nominine by David Y. Gin. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, n-BuLi

THF
RT, 95 min
96 %

This step is from the synthesis of Nominine by David Y. Gin. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, n-BuLi

THF
70 °C, 15 h
77 %

This step is from the synthesis of Retigeranic Acid by Elias J. Corey. Show me the full synthesis.

TMS₂NK

PhMe
RT, 12 h
80 %

This step is from the synthesis of Retigeranic Acid by Tomas Hudlicky. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, n-BuLi

THF
66 % (2 steps)

This step is from the synthesis of Retigeranic Acid by Paul A. Wender. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, n-BuLi

THF

This step is from the synthesis of Caribenol A by Zhen Yang. Show me the full synthesis.

TMS₂NNa

THF
-78 °C to RT, 4 h
92 %

This step is from the synthesis of Morphine by Gilbert Stork. Show me the full synthesis.

Ph₃P⁺CH₂OMe Cl^-, TMS₂NK

THF, CH₂Cl₂
-30 °C to RT, 15.5 h
95 %

This step is from the synthesis of Morphine by Gilbert Stork. Show me the full synthesis.

Ph₃P⁺CH₂OMe Cl^-, TMS₂NK

THF, CH₂Cl₂
-50 °C to RT, 15 h
74 % (2 steps)

This step is from the synthesis of Dragmacidin F by Brian M. Stoltz. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, KOt-Bu

THF
65 °C, 2 h
76 %

This step is from the synthesis of Nupharamine by Chihiro Kibayashi. Show me the full synthesis.

n-BuLi

Et₂O
0 °C to RT

This step is from the synthesis of Nupharamine by José Barluenga. Show me the full synthesis.

(COCl)₂, DMSO, Et₃N

CH₂Cl₂
-65 °C to RT, 5 h

This step is from the synthesis of Hirsutene by Takeshi Matsumoto. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, NaOt-Amyl

PhH
80 °C, 60 min
92 %

This step is from the synthesis of Hirsutene by Takeshi Matsumoto. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, NaOt-Amyl

PhH
RT, 2 h
92 %

This step is from the synthesis of Hirsutene by Shigeo Nozoe. Show me the full synthesis.

Ph₃P=CH₂

This step is from the synthesis of Hirsutene by Shigeo Nozoe. Show me the full synthesis.

Ph₃P=CH₂

DMSO
70 %

This step is from the synthesis of Hirsutene by Goverdhan Mehta. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, NaOt-Amyl

PhMe
RT to Reflux, 3 h
84 %

This step is from the synthesis of Hirsutene by R. Daniel Little. Show me the full synthesis.

Ph₃P=CH₂

This step is from the synthesis of Azadirachtin by Steven V. Ley. Show me the full synthesis.

Ph₃P⁺CHBr₂ Br^-, KOt-Bu

THF
RT, 12 h
78 % (2 steps)

This step is from the synthesis of Hirsutene by Duy H. Hua. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, NaOt-Amyl

PhMe
RT to reflux, 4 h
80 %

This step is from the synthesis of Hirsutene by Tarun K. Sarkar. Show me the full synthesis.

TMS₂NNa

THF
-78 °C to RT, ON
61 %

This step is from the synthesis of Hirsutene by Daniel D. Sternbach. Show me the full synthesis.

PhH
RT to Reflux, 6 h
81 %

This step is from the synthesis of Hirsutene by Daniel D. Sternbach. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, TMS₂NK

THF
0 °C to RT, 30 min
86 %

This step is from the synthesis of Hirsutene by Daniel D. Sternbach. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, KH

PhH, t-BuOH
RT to Reflux, 6 h
93 %

This step is from the synthesis of Coccinelline by Robert V. Stevens. Show me the full synthesis.

Ph₃P⁺CH₃ Br^-, n-BuLi

Et₂O
RT to Reflux, 90 min
82 %